2-Penten-4-yn-1-ol → [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[4-(3-hydroxy-propenyl)-[1,2,3]triazol-1-yl]-2-methyl-phenyl}-methanone

HRID 2067242Notes

Reaction equation

HRID 2067242 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:28])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:14][C:13]=2[Cl:27])=[O:11])[CH:9]=1)=[N+:2]=[N-:3].[CH2:29]([OH:34])[CH:30]=[CH:31][C:32]#[CH:33]>>[Cl:27][C:13]1[CH:14]=[C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[CH:16]=[CH:17][C:12]=1[C:10]([C:8]1[CH:9]=[C:4]([N:1]2[CH:33]=[C:32]([CH:31]=[CH:30][CH2:29][OH:34])[N:3]=[N:2]2)[CH:5]=[CH:6][C:7]=1[CH3:28])=[O:11]

Participants

3

Reactant 2

HCID 977582-Penten-4-yn-1-olHCID 86605529(5-Azido-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 68419069[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[4-(3-hydroxy-propenyl)-[1,2,3]triazol-1-yl]-2-methyl-phenyl}-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 116, using compound 434 (0.15 mmol) and pent-2-en-4-yn-1-ol (0.30 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 30:70 to 50:50 as the eluent to afford the title compound as yellow solid.

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-1dc7420f79004df7868edafa21be7e9d
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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