4-Ethynyl-5-methyl-3-phenyl-isoxazole → 2-Methyl-5-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-thiazole-4-carboxylic acid ethyl ester

HRID 1984663Notes

Reaction equation

HRID 1984663 reaction equation
[C:1]([C:3]1[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][O:6][C:7]=1[CH3:8])#[CH:2].[CH2:15]([O:17][C:18]([C:20]1[N:21]=[C:22]([CH3:26])[S:23][C:24]=1I)=[O:19])[CH3:16]>>[CH2:15]([O:17][C:18]([C:20]1[N:21]=[C:22]([CH3:26])[S:23][C:24]=1[C:2]#[C:1][C:3]1[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][O:6][C:7]=1[CH3:8])=[O:19])[CH3:16]

Participants

3

Reactant 2

HCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazoleHCID 688513165-Iodo-2-methyl-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 247844422-Methyl-5-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-thiazole-4-carboxylic acid ethyl esterYield 84%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (51 mg, 0.28 mmol) was converted (using 5-iodo-2-methyl-thiazole-4-carboxylic acid ethyl ester instead of 2-chloro-4-iodopyridine) to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 83 mg, 84%) which was obtained as a light brown solid. MS: m/e=353.2 [M+H]+.

Sources & evidence

ORD record
ord-d7aa34f4811a45c99d0fc67ae94b736d
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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