2-(propan-2-yl)-1H-1,3-benzodiazole → (E)-2-{3-fluoro-8-[(2-isopropyl-1H-benzo[d]imidazol-1-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile

HRID 869505Notes

Reaction equation

HRID 869505 reaction equation
[CH:1]([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1)([CH3:3])[CH3:2].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>>[F:28][C:25]1[CH:26]=[CH:27][C:20]2=[C:21]([CH:24]=1)[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[CH:1]([CH3:3])[CH3:2])[CH:34]=[CH:33][C:18]=1/[C:19]/2=[C:29](/[CH3:32])\[C:30]#[N:31]

Participants

3

Reactant 2

HCID 221212-(propan-2-yl)-1H-1,3-benzodiazoleHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721334(E)-2-{3-fluoro-8-[(2-isopropyl-1H-benzo[d]imidazol-1-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 98%

Procedure

Using 2-isopropyl-1H-benzo[d]imidazole (Angewandte Chemie, International Edition, 2010, vol. 9, p 1656; 89 mg, 0.56 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (200 mg, 0.56 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, the title compound (240 mg, 98%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-366ed2eabb1f4d369f80bfd206046267
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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