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

HRID 869555

Reaction equation

HRID 869555 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:36]=[CH:35][C:18]2/[C:19](=[C:29](/[CH:32]3[CH2:34][CH2:33]3)\[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>>[CH:32]1(/[C:29](=[C:19]2\[C:20]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=3[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:36]=[CH:35][C:18]\2=3)/[C:30]#[N:31])[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 216242-Propyl-1H-benzimidazoleHCID 86721388(E)-2-(8-bromomethyl-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-2-cyclopropylacetonitrile

Product 1

HCID 86721387(E)-2-cyclopropyl-2-{3-fluoro-8-[(2-propyl-1H-benzo[d]imidazol-1-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene)acetonitrileYield 92%

Procedure

Using 2-propyl-1H-benzo[d]imidazole (Synthetic Communication, 2002, vol. 32, p 3703, 55 mg, 0.33 mmol) and (E)-2-(8-bromomethyl-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-2-cyclopropylacetonitrile (120 mg, 0.31 mmol) obtained in Reference Example 6, and in the same manner as in Reference Example 1A, the title compound (132 mg, 92%) was obtained.

Workup

  1. customobtained in Reference Example 6

Sources & evidence

ORD record
ord-3c2feb50d3224f6db5df16ec81b7b6ec
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Linked notes

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