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

HRID 869560

Reaction equation

HRID 869560 reaction equation
[CH2:1]([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1)[CH2:2][CH3:3].Br[CH2:14][C:15]1[CH:35]=[CH:34][C:18]2/[C:19](=[C:30](/[CH3:33])\[C:31]#[N:32])/[C:20]3[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:21]=3[O:22][CH2:23][C:17]=2[CH:16]=1>>[F:28][C:26]1[C:25]([F:29])=[CH:24][C:21]2[O:22][CH2:23][C:17]3[CH:16]=[C:15]([CH2:14][N:8]4[C:7]5[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=5[N:5]=[C:4]4[CH2:1][CH2:2][CH3:3])[CH:35]=[CH:34][C:18]=3/[C:19](=[C:30](/[CH3:33])\[C:31]#[N:32])/[C:20]=2[CH:27]=1

Participants

3

Reactant 2

HCID 216242-Propyl-1H-benzimidazoleHCID 86721396(E)-2-[8-(bromomethyl)-2,3-difluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721395(E)-2-{2,3-difluoro-8-[(2-propyl-1H-benzo[d]imidazol-1-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 91%

Procedure

Using 2-propyl-1H-benzo[d]imidazole (Synthetic Communication, 2002, vol. 32, p 3703; 51 mg, 0.32 mmol) and (E)-2-[8-(bromomethyl)-2,3-difluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (120 mg, 0.32 mmol) obtained in Reference Example 3, and in the same manner as in Reference Example 1A, the title compound (132 mg, 91%) was obtained.

Workup

  1. customobtained in Reference Example 3

Sources & evidence

ORD record
ord-485ff65f2e5541f9972806664e5b29fd
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Linked notes

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