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

HRID 869504Notes

Reaction equation

HRID 869504 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=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>>[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[CH2:3][O:2][CH3:1])[CH:34]=[CH:33][C:18]=1/[C:19]/2=[C:29](/[CH3:32])\[C:30]#[N:31]

Participants

3

Reactant 2

HCID 2429502-(methoxymethyl)-1H-benzimidazoleHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721332(E)-2-(3-fluoro-8-{[2-(methoxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileYield 87%

Procedure

Using 2-methoxymethyl-1H-benzo[d]imidazole (Journal of Organometallic Chemistry, 2008, vol. 26, p 3889; 244 mg, 1.51 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (550 mg, 1.54 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, the title compound (576 mg, 87%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-68ac024a3b36482cbeca2e131932de7c
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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