Potassium Phosphate, Tribasic → 6-(4-Hydroxy-2-methylphenyl)benzo[d]isothiazole-3-carboxylic acid

HRID 424813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424813
Br[C:2]1[CH:13]=[CH:12][C:5]2[C:6]([C:9]([OH:11])=[O:10])=[N:7][S:8][C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])O1.[CH:30]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:28][C:23]1[CH:22]=[CH:27][C:26]([C:2]2[CH:13]=[CH:12][C:5]3[C:6]([C:9]([OH:11])=[O:10])=[N:7][S:8][C:4]=3[CH:3]=2)=[C:25]([CH3:30])[CH:24]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 534011926-Bromobenzo(d)isothiazole-3-carboxylic acid

Produkt 1

HCID 1357419876-(4-Hydroxy-2-methylphenyl)benzo[d]isothiazole-3-carboxylic acidAusbeute 273,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a degassed solution of 6-Bromo-benzo[d]isothiazole-3-carboxylic acid (0.42 g, 1.54 mmol), 3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl-phenol (0.54, 2.31 mmol), 2-Dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.064 g, 0.154 mmol), and potassium phosphate (0.71 g, 3.1 mmol) in dioxane (8 mL) and water (4 mL) is added Pd(OAc)2 (6.5 mg, 0.03 mmol). The reaction is degassed again and heated to 80 degrees for 18 h. The reaction is cooled to room temperature and concentrated under reduced pressure. The material is diluted with EtOAc and 1N HCl. The layers are separated and concentrated under reduced pressure. The crude material is diluted with 20 mL of MeOH and 2 mL H2SO4 and heated to reflux for 2 h. The reaction is concentrated onto silica and purified using a gradient of 20 to 50% EtOAc in Hexanes to yield the title compound (0.12 g, 26% yield). ES/MS m/e 300.0 (M+1).

Aufarbeitung

  1. customThe reaction is degassed again
  2. temperatureheated to 80 degrees for 18 h
  3. concentrationconcentrated under reduced pressure
  4. additionThe material is diluted with EtOAc and 1N HCl
  5. customThe layers are separated
  6. concentrationconcentrated under reduced pressure
  7. additionThe crude material is diluted with 20 mL of MeOH and 2 mL H2SO4
  8. temperatureheated
  9. temperatureto reflux for 2 h
  10. concentrationThe reaction is concentrated onto silica
  11. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-f2c09808db0e4c618473b90237f684da
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106077B2

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