1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-(3-hydroxy-1-propynyl)-,ethyl ester → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-(3-hydroxypropyl)-,ethyl ester

HRID 640708Notes

Reaction equation

HRID 640708 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([C:16]#[C:17][CH2:18][OH:19])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([CH2:16][CH2:17][CH2:18][OH:19])=[C:10]3[CH:9]=[CH:8]2)=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 686643251h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-(3-hydroxy-1-propynyl)-,ethyl ester

Product 1

HCID 686660171h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-(3-hydroxypropyl)-,ethyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-(4-fluorobenzyl)-4-(3-hydroxyprop-1-yn-1-yl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.46 g, 1.31 mmol) in MeOH (6 mL) was added palladium, (10 wt. % on activated carbon, 15 mg, 0.014 mmol). The resulting mixture was shaken in a Parr apparatus for 4 h at room temperature under H2 at 60 psi. The mixture was filtered and concentrated to afford the title product as yellow oil (0.41 g, 88% yield). LC-MS (APCl, M+H+): 357.2. HPLC: 96% purity.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-efad627edd1942beb287017307b58b12
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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