3-Aminophenylboronic acid → HCID 68907652, compound

HRID 1592814Notes

Reaction equation

HRID 1592814 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 68907652HCID 68907652, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e64a2308979d4f189d4ef5939e1f651d
Source dataset
uspto-grants-2007_11
Patent number
US07294616B2

Reaction notes

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