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

HRID 869573Notes

Reaction equation

HRID 869573 reaction equation
I[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]2=[N:4][C:3]=1[CH:13]([CH3:15])[CH3:14].[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]>>[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]([OH:36])[C:2]3[N:6]4[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]4=[N:4][C:3]=3[CH:13]([CH3:15])[CH3:14])[CH:32]=[CH:31][C:25]=1/[C:26]/2=[C:27](/[CH3:30])\[C:28]#[N:29]

Participants

3

Reactant 2

HCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileHCID 867214133-Iodo-2-isopropyl-8-methoxyimidazo[1,2-a]pyridine

Product 1

HCID 86721412(E)-2-{3-fluoro-8-[hydroxy(2-isopropyl-8-methoxyimidazo[1,2-a]pyridin-3-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 35%

Procedure

[step 3] Using 3-iodo-2-isopropyl-8-methoxyimidazo[1,2-a]pyridine (600 mg, 1.90 mmol) obtained in step 2 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (278 mg, 0.95 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 8A, step 3, (E)-2-{3-fluoro-8-[hydroxy(2-isopropyl-8-methoxyimidazo[1,2-a]pyridin-3-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (159 mg, 35%) was obtained.

Workup

  1. customobtained in Reference Example 5

Sources & evidence

ORD record
ord-be47c7a702b64a4fab62e986f2ad4353
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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