(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile → (E)-2-(3-fluoro-8-{[2-(methoxymethyl)-1H-thieno[3,4-d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile

HRID 869590Notes

Reaction equation

HRID 869590 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:8][C:7]2=[CH:9][S:10][CH:11]=[C:6]2[N:5]=1.Br[CH2:13][C:14]1[CH:33]=[CH:32][C:17]2/[C:18](=[C:28](/[CH3:31])\[C:29]#[N:30])/[C:19]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:20]=3[O:21][CH2:22][C:16]=2[CH:15]=1>>[F:27][C:24]1[CH:25]=[CH:26][C:19]2=[C:20]([CH:23]=1)[O:21][CH2:22][C:16]1[CH:15]=[C:14]([CH2:13][N:5]3[C:6]4=[CH:11][S:10][CH:9]=[C:7]4[N:8]=[C:4]3[CH2:3][O:2][CH3:1])[CH:33]=[CH:32][C:17]=1/[C:18]/2=[C:28](/[CH3:31])\[C:29]#[N:30]

Participants

3

Reactant 2

HCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrileHCID 867214402-(methoxymethyl)-1H-thieno[3,4-d]imidazole

Product 1

HCID 86721441(E)-2-(3-fluoro-8-{[2-(methoxymethyl)-1H-thieno[3,4-d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileYield 97%

Procedure

[step 2] Using 2-(methoxymethyl)-1H-thieno[3,4-d]imidazole (65 mg, 0.39 mmol) obtained in step 1 and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (141 mg, 0.39 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, the title compound (167 mg, 97%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-eafc6fb6c2ed4fc4bceb7472a64268b0
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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