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

HRID 1984658Notes

Reaction equation

HRID 1984658 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[C:17](I)=[N:18][CH:19]=[CH:20][CH:21]=1>>[Cl:15][C:16]1[C:17]([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:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 108476073-Chloro-2-iodopyridineHCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazole

Product 1

HCID 688523473-Chloro-2-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-pyridineYield 78%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (64 mg, 0.35 mmol) was converted [using 3-chloro-2-iodopyridine (prepared according to Eur. J. Org. Chem. (24), 4181, 2002) instead of 2-chloro-4-iodopyridine] to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 81 mg, 78%) which was obtained as a light yellow solid. MS: m/e=295.2/297.3 [M+H]+.

Sources & evidence

ORD record
ord-f4516dd95e814bdd9231e5afcf5bb563
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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