1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-ethynyl-1-[(4-fluorophenyl)methyl]-,ethyl ester → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-ethyl-1-[(4-fluorophenyl)methyl]-,ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:23]#[CH:24])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]>CCO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:23][CH3:24])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-ethynyl-1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (60 mg, 0.018 mmol, prepared in step 1 above) in EtOH (2 mL) was added Lindlar's catalyst (Aldrich, 20 mg). The atmosphere was vacuum degassed with hydrogen three times, and then a balloon of hydrogen was attached to the reaction. After stirring for 18 hours, the reaction was filtered through a fine filter to remove the palladium. The solvent was removed by rotary evaporation, and the crude oil was carried on without further purification. Yield 57 mg, 94%. MS (APCI): Calc: 326, Found: (M+H) 327.