4-Ethynyl-5-methyl-3-phenyl-isoxazole → HCID 178430910, compound

HRID 1984661Notes

Reaction equation

HRID 1984661 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].I[C:16]1[C:20]([CH3:21])=[CH:19][NH:18][N:17]=1>>[CH3:8][C:7]1[O:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]=1[C:1]#[C:2][C:16]1[C:20]([CH3:21])=[CH:19][NH:18][N:17]=1

Participants

3

Reactant 2

HCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazoleHCID 178430914HCID 178430914, compound

Product 1

HCID 178430910HCID 178430910, compoundYield 53%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (73 mg, 0.40 mmol) was converted [using 3-iodo-4-methyl-1H-pyrazole (prepared according to Liebigs Ann. Chem. 595, 200, 1955) instead of 2-chloro-4-iodopyridine] to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 56 mg, 53%) which was obtained as a light brown solid. MS: m/e=264.2 [M+H]+.

Sources & evidence

ORD record
ord-c8f04903e5a049589655259f06b498f3
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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