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

HRID 1515943Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(1-(3-ethoxy-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.3 g, 4.2 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 (2×20 mL). The filtrate was concentrated in vacuo. Silica gel column chromatography (30 g, ethyl acetate/petroleum ether: 1:10) afforded 2-(1-(3-ethoxy-phenyl)-3-methyl-butyl)-1H-pyrrolo[2,3-b]pyridine (800 mg, 62%) as a white solid: 1H NMR (300 MHz, CDCl3) δ ppm 9.37 (s, 1H), 8.15 (d, 1H, J=4.5 Hz), 7.83 (d, 1H, J=7.5 Hz), 7.20 (t, 1H, J=7.8 Hz), 7.01 (dd, 1H, J1=7.8 Hz, J2=4.8 Hz), 6.87-6.74 (m, 3H), 6.32 (s, 1H), 4.15 (t, 1H, J=8.1 Hz), 3.95 (q, 2H, J=6.9 Hz), 2.08-1.91 (m, 2H), 1.59-1.50 (m, 1H), 1.37 (t, 3H, J=6.9 Hz), 0.96 (s, 3H), 0.94 (s, 3H).

Workup

filtrationThe reaction mixture was filtered through a pad of celite
washwashed with methanol (2×20 mL)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-4088ce232bbb4b7ca6e00fa61d09f6c0
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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