(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile → HCID 86721480, compound

HRID 869616Notes

Reaction equation

HRID 869616 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][N:5]2[C:14]=1I.[F:16][C:17]1[CH:18]=[CH:19][C:20]2=[C:21]([CH:37]=1)[O:22][CH2:23][C:24]1[CH:34]=[C:33]([CH:35]=[O:36])[CH:32]=[CH:31][C:25]=1/[C:26]/2=[C:27](/[CH3:30])\[C:28]#[N:29]>>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][N:5]2[C:14]=1[CH:35]([OH:36])[C:33]1[CH:32]=[CH:31][C:25]2/[C:26](=[C:27](/[CH3:30])\[C:28]#[N:29])/[C:20]3[CH:19]=[CH:18][C:17]([F:16])=[CH:37][C:21]=3[O:22][CH2:23][C:24]=2[CH:34]=1

Participants

3

Reactant 2

HCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileHCID 86721481HCID 86721481, compound

Product 1

HCID 86721480HCID 86721480, compoundYield 90.6%

Procedure

[step 2] Using 2-chloro-3-iodo-7-(trifluoromethyl)imidazo[1,2-a]pyridine (1.81 g, 5.22 mmol) obtained in step 1 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (0.77 g, 2.6 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 8F, step 4, (E)-2-{8-[(2-chloro-7-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)(hydroxy)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (1.21 g, 90%) was obtained.

Workup

  1. customobtained in Reference Example 5

Sources & evidence

ORD record
ord-d60e90a6cfc74c97874cbc45880a3a28
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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