4-Ethynyl-5-methyl-3-phenyl-isoxazole → HCID 24784179, compound

HRID 1984670Notes

Reaction equation

HRID 1984670 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[N:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([CH3:21])=[CH:19][N:20]=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[N:17]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:18]([CH3:21])=[CH:19][N:20]=1

Participants

3

Reactant 2

HCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazoleHCID 68852842HCID 68852842, compound

Product 1

HCID 24784179HCID 24784179, compoundYield 21%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (92 mg, 0.50 mmol) was converted [using 2-iodo-5-methyl-1-phenyl-1H-imidazole (prepared from 5-methyl-1-phenyl-1H-imidazole by reaction of 4(5)-methyl-1-phenyl-1H-imidazole with N-iodosuccinimide in N,N-dimethylformamide at ambient temperature) instead of 2-chloro-4-iodopyridine] to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 35 mg, 21%) which was obtained as a brown solid. MS: m/e=340.2 [M+H]+.

Sources & evidence

ORD record
ord-befc431f4d0d4d98ab3b36db5df1659f
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

Loading…