3-Aminophenylboronic acid → HCID 68907652, 화합물

HRID 1592814노트

반응식

HRID 1592814 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 68907652HCID 68907652, 화합물

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매HCID 11430Potassium Carbonate용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e64a2308979d4f189d4ef5939e1f651d
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294616B2

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