2-Bromopyridine → HCID 66598131, compound

HRID 334691Notes

Reaction equation

HRID 334691 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:13]=1)[CH2:9][C:10]#[CH:11]>>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:14]2[CH:13]=[C:12]([CH2:8][CH2:9][C:10]#[C:11][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[O:16][N:15]=2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 86086770HCID 86086770, compound

Product 1

HCID 66598131HCID 66598131, compoundYield 25%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-pyridine (40 mg, 0.26 mmol) and 5-but-3-ynyl-3-(4-fluoro-phenyl)-isoxazole (55 mg, 0.26 mmol). Reaction time: 2 hours. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1 to 7:3) to yield 19 mg (65 μmol, 25%) of 2-(4-(3-(4-fluorophenyl)isoxazol-5-yl)but-1-ynyl)pyridine as a white solid (M.P.=83-84° C.).

Workup

  1. customReaction time
  2. custom2 hours
  3. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1 to 7:3)

Sources & evidence

ORD record
ord-02564cb5b0de4b15a94a7be862f92422
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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