Potassium Carbonate → HCID 58088345, compound

HRID 250286Notes

Reaction equation

HRID 250286 reaction equation
Br[CH2:2][C:3]1[C:4]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][C:12]=2[F:21])=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.[CH3:22][O:23][C:24]([C:26]1[S:30][C:29]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][C:32]=2[CH3:38])=[N:28][C:27]=1[CH3:39])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:22][O:23][C:24]([C:26]1[S:30][C:29]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:2][C:3]3[C:4]([C:11]4[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][C:12]=4[F:21])=[N:5][O:6][C:7]=3[CH:8]3[CH2:10][CH2:9]3)=[CH:33][C:32]=2[CH3:38])=[N:28][C:27]=1[CH3:39])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67271477HCID 67271477, compoundHCID 136107621HCID 136107621, compound

Product 1

HCID 58088345HCID 58088345, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromomethyl-5-cyclopropyl-3-(2-fluoro-6-trifluoromethyl-phenyl)-isoxazole (0.083 g, 0.256 mmol) and 2-(4-Hydroxy-2-methyl-phenyl)-4-methyl-thiazole-5-carboxylic acid methyl ester (0.067 g, 0.256 mmol) in 1 mL of DMF is added potassium carbonate (0.035 g, 0.256). The reaction is stirred for 60 hours. The reaction is partitioned between ethyl acetate and water. The layers are separated and the organic layer is washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue is chromatographed using a gradient of 5% ethyl acetate in hexanes to 40% ethyl acetate in hexanes to yield the title compound (0.027 g, 18%). ES/MS m/e 547.0 (M+1).

Workup

  1. customThe reaction is partitioned between ethyl acetate and water
  2. customThe layers are separated
  3. washthe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue is chromatographed

Sources & evidence

ORD record
ord-0edc1bf9d8f144ecb4169d46e061fd9c
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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