Nitrogen → (2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 38684ノート

反応式

HRID 38684 の反応式
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=1)[CH3:2].Br[C:25]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:26]=1[CH:27]=[O:28].C(=O)([O-])[O-].[K+].[K+].N#N>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.O.COCCOC>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:7]=[C:8]([C:25]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:26]=2[CH:27]=[O:28])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

参加物

8

反応物 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 70180472-Bromo-5-(trifluoromethyl)benzaldehydeHCID 58120060[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester

生成物 1

HCID 86633171(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

試薬・触媒・溶媒 3

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

反応条件

温度
85 °C

実験手順

A solution of [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (1.38 g, 4.32 mmol), 2-bromo-5-(trifluoromethyl)benzaldehyde (1.09 g, 4.32 mmol), and potassium carbonate (1.49 g, 10.8 mmol) in 2:1 DME:H2O was purged with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.499 g, 0.43 mmol) was added, and the reaction was purged with N2 for another 10 minutes, and then stirred at 85° C. overnight. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

後処理

  1. customthe reaction was purged with N2 for another 10 minutes
  2. customThe mixture was partitioned between EtOAc and H2O
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-4a4fd1b10a664708a39f54ef10ebd3be
出典データセット
uspto-grants-2013_09
特許番号
US08524748B2

反応ノート

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