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

HRID 869508Notes

Reaction equation

HRID 869508 reaction equation
[CH:1]1([C:6]2[NH:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:16][C:17]1[CH:36]=[CH:35][C:20]2/[C:21](=[C:31](/[CH3:34])\[C:32]#[N:33])/[C:22]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=3[O:24][CH2:25][C:19]=2[CH:18]=1>>[CH:1]1([C:6]2[N:7]([CH2:16][C:17]3[CH:36]=[CH:35][C:20]4/[C:21](=[C:31](/[CH3:34])\[C:32]#[N:33])/[C:22]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=5[O:24][CH2:25][C:19]=4[CH:18]=3)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 134157972-Cyclopentyl-1H-benzimidazoleHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721337(E)-2-{8-[(2-cyclopentyl-1H-benzo[d]imidazol-1-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 95.3%

Procedure

Using 2-cyclopentyl-1H-benzo[d]imidazole (62 mg, 0.335 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (120 mg, 0.335 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, the title compound (148 mg, 95%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-1669e35c746846d1a0b8d818149bb8aa
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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