Methyl 2-bromothiazole-4-carboxylate → HCID 24783924, compound

HRID 1984696Notes

Reaction equation

HRID 1984696 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].Br[C:16]1[S:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=1>>[CH3:24][O:23][C:21]([C:19]1[N:20]=[C:16]([C:2]#[C:1][C:3]2[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:5][O:6][C:7]=2[CH3:8])[S:17][CH:18]=1)=[O:22]

Participants

3

Reactant 2

HCID 2763213Methyl 2-bromothiazole-4-carboxylateHCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazole

Product 1

HCID 24783924HCID 24783924, compoundYield 70%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (92 mg, 0.50 mmol) was converted (using methyl 2-bromothiazole-4-carboxylate instead of 2-chloro-4-iodopyridine) to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 113 mg, 70%) which was obtained as a light yellow solid. MS: m/e=325.2 [M+H]+.

Sources & evidence

ORD record
ord-6f76287a38db447d8630f1452efb1106
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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