2-Chloro-5-(trifluoromethyl)pyridine → 2-(5-Trifluoromethyl-pyridin-2-yl)-benzoic acid isopropyl ester

HRID 51911

反応式

HRID 51911 の反応式
[CH:1]([O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1B(O)O)=[O:6])([CH3:3])[CH3:2].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1>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>[CH:1]([O:4][C:5](=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1)([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 53435142(2-(Isopropoxycarbonyl)phenyl)boronic acid

生成物 1

HCID 698912952-(5-Trifluoromethyl-pyridin-2-yl)-benzoic acid isopropyl ester収率 70%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

2-(Isopropylcarboxy)-phenylboronic acid (S. Caron and J. M. Hawkins, J. Org. Chem. 1998, 63, 2054-2055) (2.2 g, 10.6 mmol) and 2-chloro-5-trifluoromethylpyridine (500 mg, 2.75 mmol) were dissolved in toluene. Tetrakis(triphenylphosphine)palladium (160 mg, 0.14 mmol) was added and the reaction vessel purged by alternating vacuum and nitrogen gas three times. 8 ml of a 10% sodium carbonate solution was added and the reaction mixture was heated at reflux for 1.5 h. The resulting mixture was extracted with ethyl acetate, the combined organic layers dried (magnesium sulfate), filtered and concentrated under vacuum. Purification of the residue by column chromatography eluting with 10% ethyl acetate in hexanes provided the title compound in approximately 70% yield.

後処理

  1. customthe reaction vessel purged
  2. addition8 ml of a 10% sodium carbonate solution was added
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 1.5 h
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. dry with materialthe combined organic layers dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customPurification of the residue by column chromatography
  10. washeluting with 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-3da357480ed243f08b79952da60fad6e
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

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