Sodium Carbonate → 4-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazole

HRID 1009003Notes

Reaction equation

HRID 1009003 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:11][C:12]1[C:16](C(B(O)O)=O)=[C:15]([CH3:22])[O:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[S:9]1[CH:8]=[CH:7][C:6]2[CH:10]=[C:2]([C:16]3[C:12]([CH3:11])=[N:13][O:14][C:15]=3[CH3:22])[CH:3]=[CH:4][C:5]1=2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27765785-Bromo-1-benzothiopheneHCID 673054143,5-Dimethyl-4-isoxazoylboronic acid

Product 1

HCID 534868054-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazoleYield 60.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-1-benzothiophene (ABCR, CAS: 133150-64-8, 1.0 6 g, 5.0 mmol) in dimethoxyethane (60 mL) and ethanol (6.0 mL) was added 3,5-dimethyl-4-isoxazoylboronic acid (1.0 g, 7.5 mmol), and 2 m sodium carbonate (2.0 mL). The reaction mixture was degassed 2-3 times, tetrakis-(triphenylphosphine)palladium (0.813 g, 0.7 mmol) was added, and the mixture was stirred for 6 h at 80° C. and concentrated. The residue was taken up in water and extracted with ethyl acetate. The organics were washed, dried and concentrated. The crude product was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 4-benzo[b]thiophen-5-yl-3,5-dimethyl-isoxazole (0.69 g) as a light yellow solid. MS (ISP): m/e 230.1 (M+H)+

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-38a7e0a2adcd4b80ab7c45ce2197dfc2
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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