2-Propyl-1H-benzimidazole → (E)-2-{3,4-difluoro-8-[(2-propyl-1H-benzo[d]imidazol-1-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile

HRID 869561

Reaction equation

HRID 869561 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]=[CH:26][C:25]([F:28])=[C:24]([F:29])[C:21]=3[O:22][CH2:23][C:17]=2[CH:16]=1>>[F:28][C:25]1[CH:26]=[CH:27][C:20]2=[C:21]([C:24]=1[F:29])[O:22][CH2:23][C:17]1[CH:16]=[C:15]([CH2:14][N:8]3[C:7]4[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=4[N:5]=[C:4]3[CH2:1][CH2:2][CH3:3])[CH:35]=[CH:34][C:18]=1/[C:19]/2=[C:30](/[CH3:33])\[C:31]#[N:32]

Participants

3

Reactant 2

HCID 216242-Propyl-1H-benzimidazoleHCID 86721398(E)-2-[8-(bromomethyl)-3,4-difluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721397(E)-2-{3,4-difluoro-8-[(2-propyl-1H-benzo[d]imidazol-1-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 90%

Procedure

Using 2-propyl-1H-benzo[d]imidazole (Synthetic Communication, 2002, vol. 32, p 3703; 17 mg, 0.10 mmol) and (E)-2-[8-(bromomethyl)-3,4-difluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (40 mg, 0.12 mmol) obtained in Reference Example 4, and in the same manner as in Reference Example 1A, the title compound (41 mg, 87%) was obtained.

Workup

  1. customobtained in Reference Example 4

Sources & evidence

ORD record
ord-704a7aa2cf7448438ec79cb43a033d07
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Linked notes

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