2-Chloro-6-iodopyridine → 2-Chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-pyridine

HRID 1984667Notes

Reaction equation

HRID 1984667 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].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](I)[N:17]=1>>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([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:17]=1

Participants

3

Reactant 2

HCID 189318602-Chloro-6-iodopyridineHCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazole

Product 1

HCID 247834122-Chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-pyridineYield 87%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (92 mg, 0.50 mmol) was converted (using 2-chloro-6-iodopyridine instead of 2-chloro-4-iodopyridine) to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 129 mg, 87%) which was obtained as a light yellow oil. MS: m/e=295.1/297.3 [M+H]+.

Sources & evidence

ORD record
ord-8717929288bc4bd28642ef21c61f5b5d
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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