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

HRID 2261839노트

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HRID 2261839 반응식
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

참가 물질

8

반응물 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

생성물 1

HCID 1357419876-(4-Hydroxy-2-methylphenyl)benzo[d]isothiazole-3-carboxylic acid수율 273.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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° C. 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).

후처리

  1. customThe reaction is degassed again
  2. temperatureThe reaction is cooled to room temperature
  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

출처 및 근거

ORD 기록
ord-7e61b3b120b0400ea3739d64ce1a9321
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

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