2-cyclobutyl-1H-Benzimidazole → (E)-2-{8-[(2-cyclobutyl-1H-benzo[d]imidazol-1-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile

HRID 869507Notes

Reaction equation

HRID 869507 reaction equation
[CH:1]1([C:5]2[NH:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[N:6]=2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:15][C:16]1[CH:35]=[CH:34][C:19]2/[C:20](=[C:30](/[CH3:33])\[C:31]#[N:32])/[C:21]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=3[O:23][CH2:24][C:18]=2[CH:17]=1>>[CH:1]1([C:5]2[N:6]([CH2:15][C:16]3[CH:35]=[CH:34][C:19]4/[C:20](=[C:30](/[CH3:33])\[C:31]#[N:32])/[C:21]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=5[O:23][CH2:24][C:18]=4[CH:17]=3)[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[N:9]=2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 134157962-cyclobutyl-1H-BenzimidazoleHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721336(E)-2-{8-[(2-cyclobutyl-1H-benzo[d]imidazol-1-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 90.3%

Procedure

Using 2-cyclobutyl-1H-benzo[d]imidazole (72 mg, 0.419 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (150 mg, 0.419 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, the title compound (170 mg, 90%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-476bc7a43c134a83ace8ffab78d8afc0
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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