Potassium Carbonate → [6-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

HRID 456193

反応式

HRID 456193 の反応式
Br[C:2]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10].[CH3:19][O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(Cl)Cl.O.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>[CH3:19][O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:24]=[C:25]([C:2]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=2[CH2:4][N:5]2[CH2:9][CH2:8][O:7][C:6]2=[O:10])[C:26]([O:29][CH3:30])=[CH:27][CH:28]=1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 57576289Methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetateHCID 668919133-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one

生成物 1

HCID 66889230[6-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

3-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one (0.234 g, 0.71 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester (0.181 g, 0.59 mmol), and potassium carbonate (0.209 g, 1.48 mmol) were combined in DME (2.5 mL) and H2O (1.2 mL) and purged with N2 for 30 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.069 g, 0.06 mmol) was added, and the reaction was stirred at 90° C. for 4 hours. After cooling to room temperature, the mixture was diluted with CH2Cl2 and H2O. The aqueous layer was separated and extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

後処理

  1. customH2O (1.2 mL) and purged with N2 for 30 minutes
  2. temperatureAfter cooling to room temperature
  3. customThe aqueous layer was separated
  4. extractionextracted with CH2Cl2
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-676dbf17698d417ba949f42254c57f96
出典データセット
uspto-grants-2013_07
特許番号
US08497381B2

関連ノート

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