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

HRID 869510Notes

Reaction equation

HRID 869510 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1)[CH3:2].Br[CH2:13][C:14]1[CH:33]=[CH:32][C:17]2/[C:18](=[C:28](/[CH3:31])\[C:29]#[N:30])/[C:19]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:20]=3[O:21][CH2:22][C:16]=2[CH:15]=1>>[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:33]=[CH:32][C:17]3/[C:18](=[C:28](/[CH3:31])\[C:29]#[N:30])/[C:19]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:20]=4[O:21][CH2:22][C:16]=3[CH:15]=2)[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 158072-EthylbenzimidazoleHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721339(E)-2-{8-[(2-ethyl-1H-benzo[d]imidazol-1-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 96%

Procedure

Using 2-ethyl-1H-benzo[d]imidazole (61 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, 96%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-78b8178e77fd4dc593e0e7dd2b4f9e74
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

Loading…