2-Bromopyridine → HCID 24783669, compound

HRID 1984694Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]#[CH:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]#[C:14][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 79732-Bromopyridine

HCID 86616911HCID 86616911, compound

Product 1

HCID 24783669HCID 24783669, compoundYield 87%

Procedure

As described for example 11c, 3-(4-chloro-phenyl)-4-ethynyl-5-methyl-isoxazole (109 mg, 0.50 mmol) instead of 4-ethynyl-5-methyl-3-phenyl-isoxazole was converted (using 2-bromopyridine 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 brown solid. MS: m/e=295.1 [M+H]+.

Sources & evidence

ORD record: ord-224a43c205ea4726937bd962937e73b0
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544704B2

Reaction notes

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