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

HRID 2377099Notes

Reaction equation

HRID 2377099 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

HCID 598558491h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-ethynyl-1-[(4-fluorophenyl)methyl]-,ethyl ester

Product 1

HCID 598558221h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-ethyl-1-[(4-fluorophenyl)methyl]-,ethyl ester

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

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.

Workup

  1. customdegassed with hydrogen three times
  2. customa balloon of hydrogen was attached to the reaction
  3. filtrationthe reaction was filtered through
  4. filtrationa fine filter
  5. customto remove the palladium
  6. customThe solvent was removed by rotary evaporation
  7. customthe crude oil was carried on without further purification

Sources & evidence

ORD record
ord-864f3e8c1a4a4022b2bd7bfd934125e4
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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