1H-Indole, 2-propyl- → (E)-2-{3-fluoro-8-[(2-propyl-1H-indol-3-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile

HRID 869587Notes

Reaction equation

HRID 869587 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH3:3].[F:13][C:14]1[CH:15]=[CH:16][C:17]2=[C:18]([CH:34]=1)[O:19][CH2:20][C:21]1[CH:31]=[C:30]([CH:32]=O)[CH:29]=[CH:28][C:22]=1/[C:23]/2=[C:24](/[CH3:27])\[C:25]#[N:26]>>[F:13][C:14]1[CH:15]=[CH:16][C:17]2=[C:18]([CH:34]=1)[O:19][CH2:20][C:21]1[CH:31]=[C:30]([CH2:32][C:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[NH:5][C:4]=3[CH2:1][CH2:2][CH3:3])[CH:29]=[CH:28][C:22]=1/[C:23]/2=[C:24](/[CH3:27])\[C:25]#[N:26]

Participants

3

Reactant 2

HCID 1394151H-Indole, 2-propyl-HCID 86721404(E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile

Product 1

HCID 86721438(E)-2-{3-fluoro-8-[(2-propyl-1H-indol-3-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrileYield 55.1%

Procedure

[step 5] Using 2-propyl-1H-indole (100 mg, 0.64 mmol) obtained in step 4 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (153 mg, 0.52 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 13A, the target compound (125 mg, 55%) was obtained.

Workup

  1. customobtained in Reference Example 5

Sources & evidence

ORD record
ord-4db0b3296ee545c9881745a98ee45a25
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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