(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile → HCID 86721379, compound

HRID 869546Notes

Reaction equation

HRID 869546 reaction equation
[F:1][C:2]1[N:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:11][C:12]([CH:14]2[CH2:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.Br[CH2:19][C:20]1[CH:39]=[CH:38][C:23]2/[C:24](=[C:34](/[CH3:37])\[C:35]#[N:36])/[C:25]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:26]=3[O:27][CH2:28][C:22]=2[CH:21]=1>>[C:35](/[C:34](=[C:24]1/[C:25]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:26]=2[O:27][CH2:28][C:22]2[CH:21]=[C:20]([CH2:19][N:11]([C:5]3[C:6]([N+:8]([O-:10])=[O:9])=[N:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:12]([CH:14]3[CH2:15][CH2:16][CH2:17]3)=[O:13])[CH:39]=[CH:38][C:23]/1=2)/[CH3:37])#[N:36]

Participants

3

Reactant 2

HCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrileHCID 86721378HCID 86721378, compound

Product 1

HCID 86721379HCID 86721379, compoundYield 50%

Procedure

[step 3] Using N-(6-fluoro-2-nitropyridin-3-yl)cyclobutanecarboxamide (200 mg, 0.836 mmol) obtained in step 2 and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (250 mg, 0.697 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 1A, (E)-N-{[11-(1-cyanoethylidene)-3-fluoro-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl}-N-(6-fluoro-2-nitropyridin-3-yl)cyclobutanecarboxamide (180 mg, 50%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-445a2faf2bfa461ab72f33b8a049b94c
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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