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

HRID 1515940Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(1-(3-fluoro-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.2 g, 4.28 mmol) in methanol (35 mL) was treated with 10% palladium on carbon (180 mg). The reaction was stirred at 25° C. under hydrogen atmosphere for 16 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to afford 2-(1-(3-fluoro-phenyl)-3-methyl-butyl)-1H-pyrrolo[2,3-b]pyridine (1.2 g, 99%) as an off-white solid: 1H NMR (300 MHz, d6-DMSO): 6 ppm 11.59 (s, 1H), 8.08 (dd, 1H, J1=4.8 Hz, J2=1.5 Hz), 7.82-7.79 (m, 1H), 7.37-7.21 (m, 3H), 7.04-6.95 (m, 2H), 6.30 (s, 1H), 4.23 (t, 1H, J=8.1 Hz), 2.11-2.04 (m, 1H), 1.92-1.85 (m, 1H), 1.40-1.35 (m, 1H), 0.91 (s, 3H), 0.89 (s, 3H).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-5bcc58ca153144e7996039924a136e4a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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