(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile → (E)-2-(8-{[8-(difluoromethoxy)-2-isopropylimidazo[1,2-a]pyridin-3-yl](hydroxy)methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile

HRID 869575Notes

Reaction equation

HRID 869575 reaction equation
[F:1][CH:2]([F:17])[O:3][C:4]1[C:5]2[N:6]([C:10](I)=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)[CH:7]=[CH:8][CH:9]=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]>>[F:1][CH:2]([F:17])[O:3][C:4]1[C:5]2[N:6]([C:10]([CH:37]([OH:38])[C:35]3[CH:34]=[CH:33][C:27]4/[C:28](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:22]5[CH:21]=[CH:20][C:19]([F:18])=[CH:39][C:23]=5[O:24][CH2:25][C:26]=4[CH:36]=3)=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileHCID 867214178-(Difluoromethoxy)-3-iodo-2-isopropylimidazo[1,2-a]pyridine

Product 1

HCID 86721416(E)-2-(8-{[8-(difluoromethoxy)-2-isopropylimidazo[1,2-a]pyridin-3-yl](hydroxy)methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileYield 96.5%

Procedure

[step 3] Using 8-(difluoromethoxy)-3-iodo-2-isopropylimidazo[1,2-a]pyridine (600 mg, 1.71 mmol) obtained in step 2 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (250 mg, 0.85 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 8A, step 3, (E)-2-(8-{[8-(difluoromethoxy)-2-isopropylimidazo[1,2-a]pyridin-3-yl](hydroxy)methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (426 mg, 96%) was obtained.

Workup

  1. customobtained in Reference Example 5

Sources & evidence

ORD record
ord-6a08e376a88845529db4651a32a995ee
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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