Potassium Phosphate, Tribasic → HCID 86708290, compound

HRID 538892Notes

Reaction equation

HRID 538892 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=[O:63].[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:22]3[CH:23]=[CH:24][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:20][CH:21]=3)[S:3][C:4]=2[CH:10]=1)(=[O:63])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27343694-Methoxycarbonylphenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866818992-Bromo-6-butylbenzothiazole

Product 1

HCID 86708290HCID 86708290, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Step-4: A degassed mixture of 2-bromo-6-butylbenzo[d]thiazole (142 mg, 0.5 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (135 mg, 0.75 mmol), Pd2(dba)3 (9 mg, 0.01 mmol), Xphos (9.5 mg, 0.02 mmol), potassium phosphate (207 mg, 1.5 mmol) in dioxane (2 mL) under nitrogen atmosphere was stirred at 100° C. for 6 h. The reaction mixture was cooled to RT, evaporated and extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate and evaporated. The crude product was purified by preparative TLC to afford methyl 4-(6-butyrylbenzo[d]thiazol-2-yl)benzoate, MS (ESI+) m/z 340.2 [M+1]+

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customevaporated
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-ee5a7f86321b4f1199f62195355acbca
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

Loading…