Potassium Phosphate, Tribasic → HCID 44540525, compound

HRID 1045035Notes

Reaction equation

HRID 1045035 reaction equation
Br[C:2]1[C:10]2[S:9](=[O:12])(=[O:11])[N:8]=[C:7]([NH2:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[O:11]=[S:9]1(=[O:12])[C:10]2[C:2]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:3][CH:4]=[CH:5][C:6]=2[C:7]([NH2:13])=[N:8]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 44540523HCID 44540523, compound

Product 1

HCID 44540525HCID 44540525, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

170 mg of 7-bromo-1,1-dioxo-1H-1λ6-benzo[d]isothiazol-3-ylamine, 119 mg of phenylboronic acid, 10 mg of palladium(II)acetate, 21 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and 415 mg of potassium phosphate are suspended in 5 ml of toluene. The mixture is stirred under an argon athmosphere at 100° C. for 16 h. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and evaporated. Chromatographie of the residue with cyclohexane—ethyl acetate (1:1) affords 41 mg of 1,1-dioxo-7-phenyl-1H-1λ6-benzo[d]isothiazol-3-ylamine (P1.5).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-20e8d571aa1d47ec85b46cfb2b6459df
Source dataset
uspto-grants-2013_10
Patent number
US08563744B2

Reaction notes

Loading…