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

HRID 869554Notes

Reaction equation

HRID 869554 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.Br[CH2:14][C:15]1[CH:34]=[CH:33][C:18]2/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=3[O:22][CH2:23][C:17]=2[CH:16]=1>>[CH3:1][N:2]([CH3:12])[C:3]1[N:4]([CH2:14][C:15]2[CH:34]=[CH:33][C:18]3/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=4[O:22][CH2:23][C:17]=3[CH:16]=2)[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 17846N,N-Dimethyl-1H-benzimidazol-2-amineHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721386(E)-2-(8-{[2-(dimethylamino)-1H-benzo[d]imidazol-1-yl]methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileYield 67.1%

Procedure

[step 2] Using N,N-dimethyl-1H-benzo[d]imidazole-2-amine (57 mg, 0.35 mmol) obtained in step 1 and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (129 mg, 0.36 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, the title compound (103 mg, 66%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-2ee8b8a8be834d5dab77e1bf0ec6a1f2
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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