(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile → (E)-2-(8-{[7-chloro-2-(methoxymethyl)imidazo[1,2-a]pyridin-3-yl](hydroxy)methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile

HRID 869577Notes

Reaction equation

HRID 869577 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](I)=[C:9]([CH2:11][O:12][CH3:13])[N:10]=[C:4]2[CH:3]=1.[F:15][C:16]1[CH:17]=[CH:18][C:19]2=[C:20]([CH:36]=1)[O:21][CH2:22][C:23]1[CH:33]=[C:32]([CH:34]=[O:35])[CH:31]=[CH:30][C:24]=1/[C:25]/2=[C:26](/[CH3:29])\[C:27]#[N:28]>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([CH:34]([OH:35])[C:32]3[CH:31]=[CH:30][C:24]4/[C:25](=[C:26](/[CH3:29])\[C:27]#[N:28])/[C:19]5[CH:18]=[CH:17][C:16]([F:15])=[CH:36][C:20]=5[O:21][CH2:22][C:23]=4[CH:33]=3)=[C:9]([CH2:11][O:12][CH3:13])[N:10]=[C:4]2[CH:3]=1

Participants

3

Reactant 2

HCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileHCID 867214217-Chloro-3-iodo-2-(methoxymethyl)imidazo[1,2-a]pyridine

Product 1

HCID 86721420(E)-2-(8-{[7-chloro-2-(methoxymethyl)imidazo[1,2-a]pyridin-3-yl](hydroxy)methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrileYield 75%

Procedure

[step 4] Using 7-chloro-3-iodo-2-(methoxymethyl)imidazo[1,2-a]pyridine (700 mg, 2.17 mmol) obtained in step 3 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (318 mg, 1.09 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 8F, step 4, (E)-2-(8-{[7-chloro-2-(methoxymethyl)imidazo[1,2-a]pyridin-3-yl](hydroxy)methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (400 mg, 75%) was obtained.

Workup

  1. customobtained in Reference Example 5

Sources & evidence

ORD record
ord-b26904e181134258853d9714f4efd497
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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