(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile → HCID 86721422, compound

HRID 869578Notes

Reaction equation

I[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:5]2=[N:4][C:3]=1[CH2:15][O:16][CH3:17].[F:18][C:19]1[CH:20]=[CH:21][C:22]2=[C:23]([CH:39]=1)[O:24][CH2:25][C:26]1[CH:36]=[C:35]([CH:37]=[O:38])[CH:34]=[CH:33][C:27]=1/[C:28]/2=[C:29](/[CH3:32])\[C:30]#[N:31]>>[F:18][C:19]1[CH:20]=[CH:21][C:22]2=[C:23]([CH:39]=1)[O:24][CH2:25][C:26]1[CH:36]=[C:35]([CH:37]([OH:38])[C:2]3[N:6]4[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:5]4=[N:4][C:3]=3[CH2:15][O:16][CH3:17])[CH:34]=[CH:33][C:27]=1/[C:28]/2=[C:29](/[CH3:32])\[C:30]#[N:31]

Participants

Reactant 2

HCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile

HCID 86721423HCID 86721423, compound

Product 1

HCID 86721422HCID 86721422, compoundYield 82%

Procedure

[step 4] Using 3-iodo-2-(methoxymethyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridine (700 mg, 1.97 mmol) obtained in step 3 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (288 mg, 0.98 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 8F, step 4, (E)-2-(3-fluoro-8-{hydroxy[2-(methoxymethyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (420 mg, 82%) was obtained.

Workup

customobtained in Reference Example 5

Sources & evidence

ORD record: ord-a5233f1748374e13ace7ba4d5865393d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969345B2

Reaction notes

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