2-Bromopyridine → HCID 68850417, compound

HRID 1984693Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]#[CH:16])=[C:13]([CH3:17])[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]#[C:16][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[C:13]([CH3:17])[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Reactant 2

HCID 79732-Bromopyridine

HCID 86616910HCID 86616910, compound

Product 1

HCID 68850417HCID 68850417, compoundYield 72%

Procedure

As described for example 11c, 3-(3-chloro-4-methoxy-phenyl)-4-ethynyl-5-methyl-isoxazole (134 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, 117 mg, 72%) which was obtained as a white solid. MS: m/e=325.2 [M+H]+.

Sources & evidence

ORD record: ord-10bedb4d19a643389a9b06f689003717
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544704B2

Reaction notes

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