{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester → {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester

HRID 1515853Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([C:17]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=3)=[CH:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[NH:14][C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([CH:17]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=3)[CH2:18][CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[NH:14][C:11]2=[N:12][CH:13]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester (582 mg, 1.21 mmol) and 10% palladium on activated carbon (0.6 g) in methanol (200 mL) was heated at 50° C. under hydrogen (5 atm) for 5 h. After cooling, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo to give {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester (584 mg) which was used in the next step without purification: LC/MS m/e calcd for C26H33N3O4S [M+H]+ 484.63, observed 484.2.

Workup

temperatureAfter cooling
customthe catalyst was removed by filtration
washwashed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-a8d492aa21854599a0655db3fa44dc12
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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