4-chloro-2-cyclopropyl-1H-benzo[d]imidazole → (E)-2-{8-[(4-chloro-2-cyclopropyl-1H-benzo[d]imidazol-1-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}-2-cyclopropylacetonitrile

HRID 869557Notes

Reaction equation

HRID 869557 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH:11]3[CH2:13][CH2:12]3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[CH2:15][C:16]1[CH:37]=[CH:36][C:19]2/[C:20](=[C:30](/[CH:33]3[CH2:35][CH2:34]3)\[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>>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH:11]3[CH2:13][CH2:12]3)[N:7]([CH2:15][C:16]3[CH:37]=[CH:36][C:19]4/[C:20](=[C:30](/[CH:33]5[CH2:34][CH2:35]5)\[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:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 609787924-chloro-2-cyclopropyl-1H-benzo[d]imidazoleHCID 86721388(E)-2-(8-bromomethyl-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-2-cyclopropylacetonitrile

Product 1

HCID 86721390(E)-2-{8-[(4-chloro-2-cyclopropyl-1H-benzo[d]imidazol-1-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}-2-cyclopropylacetonitrileYield 74.8%

Procedure

Using 4-chloro-2-cyclopropyl-1H-benzo[d]imidazole (EP1988091, 60 mg, 0.31 mmol) and (E)-2-(8-bromomethyl-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-2-cyclopropylacetonitrile (120 mg, 0.31 mmol) obtained in Reference Example 6, and in the same manner as in Reference Example 1A, the title compound (115 mg, 74%) was obtained.

Workup

  1. customobtained in Reference Example 6

Sources & evidence

ORD record
ord-23f2afecee18464488149da6a72e37d7
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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