(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile → HCID 86721432, compound

HRID 869584Notes

Reaction equation

HRID 869584 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:9]=[CH:8][N:7]3[C:16]=2I)[CH2:3][CH2:2]1.[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]>>[CH:1]1([C:4]2[N:5]=[C:6]3[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:9]=[CH:8][N:7]3[C:16]=2[CH:37]([OH:38])[C:35]2[CH:34]=[CH:33][C:27]3/[C:28](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:22]4[CH:21]=[CH:20][C:19]([F:18])=[CH:39][C:23]=4[O:24][CH2:25][C:26]=3[CH:36]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileHCID 86721433HCID 86721433, compound

Product 1

HCID 86721432HCID 86721432, compoundYield 100.8%

Procedure

[step 3] Using 2-cyclopropyl-3-iodo-8-(trifluoromethyl)imidazo[1,2-a]pyridine (480 mg, 1.36 mmol) obtained in step 2 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (200 mg, 0.68 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 8A, step 3, (E)-2-(8-{[2-cyclopropyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl](hydroxy)methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (356 mg) was obtained quantitatively.

Workup

  1. customobtained in Reference Example 5

Sources & evidence

ORD record
ord-6957d8930f744cc2a88cf33d3f330c32
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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