1-(3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone → 1-{3-[3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-butyl]-phenyl}-ethanone

HRID 1515949Notes

Reaction equation

[CH3:1][CH:2]([CH3:23])[CH:3]=[C:4]([C:14]1[CH:15]=[C:16]([C:20](=[O:22])[CH3:21])[CH:17]=[CH:18][CH:19]=1)[C:5]1[NH:13][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1>CO.O1CCCC1.[Pd]>[CH3:1][CH:2]([CH3:23])[CH2:3][CH:4]([C:14]1[CH:15]=[C:16]([C:20](=[O:22])[CH3:21])[CH:17]=[CH:18][CH:19]=1)[C:5]1[NH:13][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1-(3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone (0.85 g, 2.8 mmol) in methanol (20 mL) and tetrahydrofuran (30 mL) was treated with 10% palladium on carbon (300 mg). The reaction was stirred for 16 h at 25° C. under hydrogen atmosphere. At this time, the reaction mixture was filtered. The filtrate was concentrated in vacuo. Silica gel column chromatography (20 g, 200-300 mesh, 10% ethyl acetate/petroleum ether) afforded 1-{3-[3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-butyl]-phenyl}-ethanone (0.50 g, 58.3%) as an off-white solid: 1H NMR (300 MHz, d6-DMSO) δ ppm 11.63 (s, 1H), 8.09 (d, 1H, J=3.6 Hz), 7.96 (s, 1H), 7.81 (d, 2H, J=7.5 Hz), 7.66 (d, 1H, J=7.5 Hz), 7.46 (t, 1H, J=7.5 Hz), 6.98 (dd, 1H, J1=4.5 Hz, J2=8.1 Hz), 6.31 (s, 1H), 4.30 (t, 1H, J=8.1 Hz), 2.57 (s, 3H), 2.17-2.10 (m, 1H), 1.91-1.86 (m, 1H), 1.41-1.39 (m, 1H), 0.92 (s, 3H), 0.90 (s, 3H).

Workup

filtrationAt this time, the reaction mixture was filtered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-59b6af021531497ea4e07e3f1a5c44ad
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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