3-Butyn-1-OL → [2-Chloro-4-(4-methoxy-phenylamino)-phenyl]-{5-[4-(2-hydroxy-ethyl)-[1,2,3]triazol-1-yl]-2-methyl-phenyl}-methanone

HRID 2067264Notes

Reaction equation

HRID 2067264 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]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:14][C:13]=2[Cl:27])=[O:11])[CH:9]=1)=[N+:2]=[N-:3].[CH2:29]([OH:33])[CH2:30][C:31]#[CH:32]>>[Cl:27][C:13]1[CH:14]=[C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:16]=[CH:17][C:12]=1[C:10]([C:8]1[CH:9]=[C:4]([N:1]2[CH:32]=[C:31]([CH2:30][CH2:29][OH:33])[N:3]=[N:2]2)[CH:5]=[CH:6][C:7]=1[CH3:28])=[O:11]

Participants

3

Reactant 2

HCID 135663-Butyn-1-OLHCID 86605534(5-Azido-2-methyl-phenyl)-[2-chloro-4-(4-methoxy-phenylamino)-phenyl]-methanone

Product 1

HCID 11712360[2-Chloro-4-(4-methoxy-phenylamino)-phenyl]-{5-[4-(2-hydroxy-ethyl)-[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 448 (0.03 mmol) and but-3-yn-1-ol (0.06 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 30:70 to 100:0 as the eluent to afford the title compound. 13C NMR (CDCl3) δ 194.7, 157.3, 150.5, 146.2, 141.4, 138.1, 135.8, 134.6, 134.2, 132.5, 132.2, 126.5, 125.3, 122.1, 120.6, 120.1, 115.2, 115.0, 111.8, 61.5, 55.6, 28.6, 19.9

Workup

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

Sources & evidence

ORD record
ord-ee5abcb455bd4837b1c019d7d5798766
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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