HCID 67229113, compound → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

HRID 1515716Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (2.5 g, 5.89 mmol) and 10% palladium on activated carbon (900 mg) in methanol (600 mL) was heated at 50° C. under 50 bar of hydrogen in a steel bomb for 5 h. The mixture was cooled to 25° C., the solids filtered off, washed with ethyl acetate and concentrated in vacuo to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (1.7 g, 68%) as a white solid which was used without further purification: LC/MS m/e calcd for C23H26N2O4S [M+H]+ 427.54, observed 426.8; 1H NMR (400 MHz, CDCl3) δ ppm 10.81 (br. s., 1H), 8.79 (br. s., 1H), 8.56 (s, 1H), 7.88-7.93 (m, J=8.3 Hz, 2H), 7.48-7.53 (m, J=8.1 Hz, 2H), 6.48 (s, 1H), 5.31 (s, 1H), 4.30 (t, J=7.7 Hz, 1H), 3.99 (s, 3H), 3.03 (s, 3H), 2.12-2.33 (m, 2H), 1.59-1.86 (m, 4H), 1.45-1.56 (m, 2H), 1.15-1.29 (m, 2H).

Workup

filtrationthe solids filtered off
washwashed with ethyl acetate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2c79dc0841be4423b3c1e6b286f856b5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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