2-(3-methyl-1-m-tolylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridine → 2-(3-methyl-1-m-tolylbutyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515934Notes

Reaction equation

[CH3:1][CH:2]([CH3:21])[CH:3]=[C:4]([C:12]1[NH:20][C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH:13]=1)[C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1>O1CCCC1.CO.[Pd]>[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([C:12]1[NH:20][C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH:13]=1)[C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(3-methyl-1-m-tolylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.30 g, 4.70 mmol) in tetrahydrofuran (20 mL) and methanol (40 mL) was treated with 10% palladium on carbon (260 mg). The reaction was stirred at 25° C. under hydrogen atmosphere for 2 d. The reaction mixture was filtered and washed with tetrahydrofuran (2×15 mL). The filtrate was concentrated in vacuo. Silica gel column chromatography (300-400 mesh, 11% ethyl acetate/petroleum ether) afforded 2-(3-methyl-1-m-tolylbutyl)-1H-pyrrolo[2,3-b]pyridine (1.07 g, 81.3%) as light oil: 1H NMR (300 MHz, d6-DMSO): δ ppm 11.54 (s, 1H), 8.09 (d, 1H, J=3.6 Hz), 7.80 (d, 1H, J=7.5 Hz), 7.19-7.16 (m, 3H), 6.98-6.94 (m, 2H), 6.26 (d, 1H, J=1.5 Hz), 4.13 (t, 1H, J=8.1 Hz), 2.27 (s, 3H), 2.09-2.05 (m, 1H), 1.86-1.81 (m, 1H), 1.41-1.36 (m, 1H), 0.90 (s, 3H), 0.89 (s, 3H.

Workup

filtrationThe reaction mixture was filtered
washwashed with tetrahydrofuran (2×15 mL)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-24d52690fbdc48acb30d3b421267c7a8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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