3-Aminophenylboronic acid → HCID 68907652、化合物

HRID 1592814ノート

反応式

HRID 1592814 の反応式
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[Cl:7].[NH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1>C(COC)OC.C(=O)([O-])[O-].[K+].[K+]>[Cl:7][C:3]1[S:4][CH:5]=[CH:6][C:2]=1[C:13]1[CH:14]=[C:9]([NH2:8])[CH:10]=[CH:11][CH:12]=1

参加物

5

反応物 2

HCID 922693-Aminophenylboronic acidHCID 27245593-Bromo-2-chlorothiophene

生成物 1

HCID 68907652HCID 68907652、化合物

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 11430Potassium Carbonate溶媒

反応条件

温度
90 °C

実験手順

3-bromo-2-chlorothiophene (1.00 mL), 3-aminophenylboronic acid (2.2266 g) and palladium tetrakistriphenylphosphine (544.8 mg) were combined in a mixture of 40 mL of dimethoxyethane and 15 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90° C. overnight. The reaction mixture was then cooled to room temperature and partitioned between EtOAc and water. The EtOAc layer was then dried over MgSO4, filtered and concentrated under vacuum. The resulting residue was purified using silica gel chromatography eluting with a 1:1 solution of DCM/Hexanes, followed by a 4:3 solution of DCM/Hexanes and finally a 2:1 solution of DCM/Hexanes, to give 1.80 g of 3-(2-chlorothiophen-3-yl)benzenamine.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. dry with materialThe EtOAc layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was purified
  7. washeluting with a 1:1 solution of DCM/Hexanes

出典と根拠

ORDレコード
ord-e64a2308979d4f189d4ef5939e1f651d
出典データセット
uspto-grants-2007_11
特許番号
US07294616B2

反応ノート

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