5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine → 5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-butyl]-1H-pyrrolo[2,3-b]pyridine

HRID 1515834Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (600 mg, 1.67 mmol) and 10% palladium on activated carbon (180 mg) in methanol (300 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to 25° C., the solids filtered off, washed with ethyl acetate and concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-butyl]-1H-pyrrolo[2,3-b]pyridine (380 mg, 63%) as a white solid: LC/MS m/e calcd for C19H21FN2O2S [M+H]+ 361.45, observed 361.0; 1H NMR (400 MHz, CDCl3) δ ppm 11.77 (br. s., 1H), 8.16 (br. s., 1H), 7.97-8.01 (m, 1H), 7.90 (d, J=8.1 Hz, 2H), 7.52-7.60 (m, 2H), 6.52 (s, 1H), 4.45 (t, J=7.8 Hz, 1H), 3.03-3.07 (m, 3H), 1.98-2.16 (m, 2H), 1.50 (dt, J=13.5, 6.6 Hz, 1H), 0.95-1.02 (m, 6H).

Workup

temperatureThe mixture was cooled to 25° C.
filtrationthe solids filtered off
washwashed with ethyl acetate
concentrationconcentrated in vacuo
customPurification

Sources & evidence

ORD record: ord-03b2a0443b254800b2295f69301288c5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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