4-(Tri-n-butylstannyl)thiazole → HCID 22316815, compound

HRID 1597575Notes

Reaction equation

HRID 1597575 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:15]([F:23])[CH:14]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:30]1[N:31]=[CH:32][S:33][CH:34]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:15]1[CH:14]=[C:13]([C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:30]4[N:31]=[CH:32][S:33][CH:34]=4)=[CH:3][CH:4]=3)=[N:9][O:10][C:11]=2[CH3:24])[CH:18]=[CH:17][C:16]=1[S:19]([CH3:22])(=[O:21])=[O:20]

Participants

5

Reactant 2

HCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 22316936HCID 22316936, compound

Product 1

HCID 22316815HCID 22316815, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-(4-bromophenyl)-4-[3-fluoro-4-(methylsulfonyl)phenyl]-5-methylisoxazole (219 mg, 0.53 mmol), tributyl(1,3-thiazol-4-yl)tin (200 mg, 0.53 mmol) and tetrakis(triphenylphosphine)palladium (62 mg, 0.053 mmol) in toluene (5 ml) was refluxed for 26 h. The mixture was evaporated and the obtained residue was chromatographed on a column of silica gel (40 g) as eluting with ethyl acetate/hexane (1/2) to give 198 mg of a white solid, which was recrystallized from ethyl acetate/hexane to afford 128 mg (58%) of the title compound.

Workup

  1. temperaturewas refluxed for 26 h
  2. customThe mixture was evaporated
  3. customthe obtained residue was chromatographed on a column of silica gel (40 g)
  4. washas eluting with ethyl acetate/hexane (1/2)

Sources & evidence

ORD record
ord-aa5114919c03444d9fab33f8123a421f
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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