Ethanol → HCID 66790844, compound

HRID 1510165Notes

Reaction equation

HRID 1510165 reaction equation
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].O.C(O)C.B(O)(O)[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[CH:16][CH:15]=1>C1C=CC=CC=1>[CH:23]([S:20]([C:17]1[CH:18]=[CH:19][C:14]([C:2]2[C:3]([NH2:4])=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:15][CH:16]=1)(=[O:21])=[O:22])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 702EthanolHCID 962Water2×HCID 119922-BromoanilineHCID 441193274-(Isopropylsulphonyl)benzeneboronic acid

Product 1

HCID 66790844HCID 66790844, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-bromoaniline (1.51 g, 8.78 mmol) in a mixture of benzene (58 mL), H2O (23 mL) and ethanol (3 mL) was added 4-(isopropylsulfonylphenyl)boronic acid (3.00 g, 13.2 mmol) followed by tetrakis(triphenylphoshine) palladium(0) (1.01 g, 0.88 mmol). After stirring 85° C. for 48 h the reaction mixture was poured into H2O (500 mL), extracted with chloroform (three times), dried over MgSO4 and concentrated under vacuum. Purification by silica gel chromatography (20% EtOAc/hexanes—40% EtOAc/hexanes) afforded the desired product.

Workup

  1. extractionextracted with chloroform (three times)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel chromatography (20% EtOAc/hexanes—40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-604c38329e3f497eafb4af416ea731f1
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

Loading…