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

HRID 869564Notes

Reaction equation

HRID 869564 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[C:12]=1I)([CH3:3])[CH3:2].[F:14][C:15]1[CH:16]=[CH:17][C:18]2=[C:19]([CH:35]=1)[O:20][CH2:21][C:22]1[CH:32]=[C:31]([CH:33]=[O:34])[CH:30]=[CH:29][C:23]=1/[C:24]/2=[C:25](/[CH3:28])\[C:26]#[N:27]>>[F:14][C:15]1[CH:16]=[CH:17][C:18]2=[C:19]([CH:35]=1)[O:20][CH2:21][C:22]1[CH:32]=[C:31]([CH:33]([OH:34])[C:12]3[N:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]4=[N:5][C:4]=3[CH:1]([CH3:3])[CH3:2])[CH:30]=[CH:29][C:23]=1/[C:24]/2=[C:25](/[CH3:28])\[C:26]#[N:27]

Participants

3

Reactant 2

HCID 584591402-Isopropyl-3-iodoimidazo[1,2-a]pyridineHCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile

Product 1

HCID 86721403(E)-2-{3-fluoro-8-[hydroxy(2-isopropylimidazo[1,2-a]pyridin-3-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 45.2%

Procedure

[step 3] Using 2-isopropyl-3-iodoimidazo[1,2-a]pyridine (366 mg, 1.28 mmol) obtained in step 2 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (250 mg, 0.853 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-isopropylimidazo[1,2-a]pyridin-3-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (175 mg, 45%) was obtained.

Workup

  1. customobtained in Reference Example 5

Sources & evidence

ORD record
ord-55885fc58f1241339277594f5d03c023
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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