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

HRID 869509Notes

Reaction equation

HRID 869509 reaction equation
[CH:1]1([CH2:4][C:5]2[NH:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[N:6]=2)[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([CH2:4][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]1

Participants

3

Reactant 2

HCID 223799252-(cyclopropylmethyl)-1H-benzo[d]imidazoleHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721338(E)-2-(8-{[2-(cyclopropylmethyl)-1H-benzo[d]imidazol-1-yl]methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileYield 93%

Procedure

Using 2-cyclopropylmethyl-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 (175 mg, 93%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-0dfa0613ab1841cd83e43383adcfd365
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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