2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-but-1-enyl]-benzoic acid methyl ester → 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butyl]-benzoic acid methyl ester

HRID 1515843Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-but-1-enyl]-benzoic acid methyl ester (660 mg, 1.85 mmol) and 10% palladium on activated carbon (198 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 16 h. The mixture was cooled to 25° C., the solids filtered off, washed with ethyl acetate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 20% ethyl acetate/hexanes) afforded 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butyl]-benzoic acid methyl ester (658 mg, 97%): LC/MS m/e calcd for C20H20F2N2O2 [M+H]+ 385.43, observed 384.9.

Workup

temperatureThe mixture was cooled to 25° C.
filtrationthe solids filtered off
washwashed with ethyl acetate
concentrationconcentrated in vacuo
customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-c955f3ca89964aa9bd3212ca8de163b2
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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