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6th September 2013 @ 14:54

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Reaction information

*#Reaction file
reactionscheme_40d.cdx
*Reaction file type CDX
*Procedure

To a 30 mL Schlenk vial under argon at room temperature was added dppf (68.1 mg, 0.13 mmol), sodium propane-2-thiolate (0.51 g, 5.0 mmol), PhBr (0.21 g, 1.3 mmol) and BnNC (0.22 mL, 2.0 mmol). PdCl2 (12.8 mg, 0.072 mmol) was then added against a counterflow of argon. Finally, toluene (13 mL) was used to wash all solids from the sides of the vial, which was then heated at 109 °C in a Stem block. The reaction mixture was allowed to cool to room temperature before ether (10 mL) and concentrated aqueous potassium hydroxide solution (5 mL) were added. The aqueous layer was extracted with ether (3x15 mL). The combined organics were dried over MgSO4, filtered and evaporated. Further purification on silica with petrol:ether (4:1) gave the title compound as a pale-yellow oil, (0.13 g, 40%), found to consist of two isomers by NMR in a ratio of 1 : 2.

*Yield (%) 40 %
*Type of Yield Isolated pure product
Reference(s)
Gustaf Saluste p122-123.pdf
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Overall reaction? True
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6th September 2013 @ 12:34

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Reaction information

*#Reaction file
reactionscheme_40c.cdx
*Reaction file type CDX
*Procedure

To a 30 mL Schlenk vial under argon at room temperature was added dppf (66.8 mg, 0.13 mmol), sodium propane-2-thiolate (0.50 g, 5.0 mmol), PhBr (0.20 g, 1.3 mmol) and n-BuNC (0.20 mL, 2.0 mmol). PdCl2 (12.5 mg, 0.072 mmol) was then added against a counterflow of argon. Finally, toluene (13 mL) was used to wash all solids from the sides of the vial, which was then heated at 109 °C in a Stem block for 5 h. The reaction mixture was allowed to cool to room temperature before ether (10 mL) and concentrated aqueous potassium hydroxide solution (5 mL) were added. The aqueous layer was extracted with ether (3x15 mL). The combined organics were dried over MgSO4, filtered and evaporated. Further purification on silica with petrol:ether (2:1) gave the title compound as a pale-yellow oil, (0.19 g, 62%), found to consist of two isomers in a ratio of 3.7 : 1 by NMR.

*Yield (%) 62 %
*Type of Yield Isolated pure product
Reference(s)
Gustaf Saluste p121-122.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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5th September 2013 @ 12:22

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Reaction information

*#Reaction file
overallscheme_31b.cdx
*Reaction file type CDX
*Procedure See child reaction steps
*Yield (%)  
*Type of Yield  
Reference(s)
Gustaf Saluste p106-107.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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Reaction 23b: Palladium-Catalytic synthesis of N-(tert-butyl)-N [1-phenyl-1-tetrahydro-1H-1-pyrrolylmethylidene]amine

Reaction 31B: Synthesis by tert-butyl deprotection of phenyl(tetrahydro-1H-1-pyrrolyl)methanimine

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3rd September 2013 @ 13:19

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Reaction information

*#Reaction file
reactionscheme_33i (2).cdx
*Reaction file type CDX
*Procedure

Dry Cs2CO3 (0.81 g, 2.5 mmol), dppf (0.11 g, 0.20 mmol),4-bromoacetophenone (0.40 g, 2.0 mmol) and morpholine (0.73 g, 0.010 mol) were added to a 30 mL Schlenk tube under argon. Dry, de-gassed toluene (10 mL) was added, followed by tBuNC (0.34 mL, 3.0 mmol) and finally PdCl(19.8 mg, 0.11 mmol) was added against a flow of argon. Another aliquote of toluene (10 mL) was added and the tube fitted with a stopper. The mixture was heated with stirring at 109 °C for 5 h. After cooling to room temperature, the reaction mixture was added to ether (20 mL) and the resulting slurry was filtered and extracted with dilute acetic acid (2.5% in water, 6x5 mL). The combined aqueous extractions were washed with ether (2x10 mL), then treated with a concentrated KOH-solution (30 mL) in presence of ether (20 mL). The ethereal layer was collected and the aqueous layer extracted with ether (3x30 mL). The combined ether phases were dried over MgSO4 before evaporation. Work-up followed by Kugelrohr-distillation gave the title compound as yellow crystals, (0.35 g, 62%), m.p. 102-104 oC.

*Yield (%) 62 %
*Type of Yield Isolated pure product
Reference(s)
Gustaf Saluste p98.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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3rd September 2013 @ 11:59

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Reaction information

*#Reaction file
reactionscheme_32i(1).cdx
*Reaction file type CDX
*Procedure

Dry Cs2CO3 (0.84 g, 2.6 mmol), dppf (0.11 g, 0.20 mmol), 3-bromopyridine (0.32 g, 2.0 mmol) and pyrrolidine (0.73 g, 0.011 mol) were added to a 30 mL Schlenk tube under argon. Dry, de-gassed toluene (10 mL) was added, followed by tBuNC (0.34 mL, 3.0 mmol) and finally PdCl(19.6 mg, 0.11 mmol) was added against a flow of argon. Another aliquote of toluene (10 mL) was added and the tube fitted with a stopper. The mixture was heated with stirring at 109 °C for 5 h. After cooling to room temperature, the reaction mixture was added to ether (20 mL) and the resulting slurry filtered to give a dark-brown solution which was extracted with dilute acetic acid (2.5% in water, 6x5 mL). The combined aqueous extractions were washed with ether (2x10 mL), then treated with a concentrated KOH-solution (30 mL) in presence of ether (20 mL). The ethereal layer was collected and the aqueous layer extracted with ether (3x30 mL). The combined ether phases were dried over MgSO4 before evaporation. Kugelrohr-distillation (oven temp 105-110 oC / 1 mmHg) gave the title compound as a transparent oil which crystallised in the freezer to give a white solid, (0.33 g, 71%), m.p. 28-30 oC

*Yield (%) 71 %
*Type of Yield Isolated pure product
Reference(s)
Gustaf Saluste p92-93.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files