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

HRID 1515946Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(1-(3-methoxy-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.3 g, 4.5 mmol) in methanol (30 mL) was treated with 10% palladium on carbon (130 mg). The reaction was stirred for 16 h at 25° C. under a balloon filled with hydrogen gas. The reaction mixture was filtered through a pad of celite and washed with methanol (2×30 mL). The filtrate was concentrated in vacuo. Silica gel column chromatography (20 g, petroleum ether/ethyl acetate 15:1) afforded 2-(1-(3-methoxy-phenyl)-3-methyl-butyl)-1H-pyrrolo[2,3-b]pyridine (900 mg, 68%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 10.54 (br. s., 1H), 8.16 (t, 1H, J=3.6 Hz), 7.83 (d, 1H, J=7.8 Hz), 7.24 (t, 1H, J=8.1 Hz), 7.02 (dd, 1H, J1=7.8 Hz, J2=4.8 Hz), 6.91-6.74 (m, 3H), 6.32 (s, 1H), 4.20 (t, 1H, J=7.5 Hz), 3.73 (s, 3H), 2.10-1.95 (m, 2H), 1.60-1.51 (m, 1H), 0.96 (d, 3H, J=4.2 Hz), 0.89 (s, 3H, J=4.2 Hz).

Workup

filtrationThe reaction mixture was filtered through a pad of celite
washwashed with methanol (2×30 mL)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-dc210a4bdec5459a9a52799307ad5371
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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