ethyl 2-bromo-1,4-dimethyl-1H-imidazole-5-carboxylate → HCID 23624254, compound

HRID 1984687Notes

Reaction equation

HRID 1984687 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]([CH3:27])[C:22](Br)=[N:23][C:24]=1[CH3:25])=[O:19])[CH3:16]>>[CH2:15]([O:17][C:18]([C:20]1[N:21]([CH3:27])[C:22]([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])=[N:23][C:24]=1[CH3:25])=[O:19])[CH3:16]

Participants

3

Reactant 2

HCID 13897513ethyl 2-bromo-1,4-dimethyl-1H-imidazole-5-carboxylateHCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazole

Product 1

HCID 23624254HCID 23624254, compoundYield 63%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (92 mg, 0.50 mmol) was converted (using 2-bromo-3,5-dimethyl-3H-imidazole-4-carboxylic acid ethyl ester instead of 2-chloro-4-iodopyridine) to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 110 mg, 63%) which was obtained as a light yellow solid. MS: m/e=350.3 [M+H]+.

Sources & evidence

ORD record
ord-61944f54ffa04534ae067488f62dc24b
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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