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

HRID 869514Notes

Reaction equation

HRID 869514 reaction equation
[F:1][C:2]1([F:15])[CH2:5][CH:4]([C:6]2[NH:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=2)[CH2:3]1.Br[CH2:17][C:18]1[CH:37]=[CH:36][C:21]2/[C:22](=[C:32](/[CH3:35])\[C:33]#[N:34])/[C:23]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=3[O:25][CH2:26][C:20]=2[CH:19]=1>>[F:15][C:2]1([F:1])[CH2:3][CH:4]([C:6]2[N:7]([CH2:17][C:18]3[CH:37]=[CH:36][C:21]4/[C:22](=[C:32](/[CH3:35])\[C:33]#[N:34])/[C:23]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=5[O:25][CH2:26][C:20]=4[CH:19]=3)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH2:5]1

Participants

3

Reactant 2

HCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrileHCID 867213422-(3,3-difluorocyclobutyl)-1H-benzo[d]imidazole

Product 1

HCID 86721343(E)-2-(8-{[2-(3,3-difluorocyclobutyl)-1H-benzo[d]imidazol-1-yl]methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileYield 96.9%

Procedure

[step 3] Using 2-(3,3-difluorocyclobutyl)-1H-benzo[d]imidazole (57 mg, 0.27 mmol) obtained in step 2 and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (100 mg, 0.28 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, the title compound (127 mg, 96%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-9ccd2ce19d3142bc8fb500d43aa40190
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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