Water → 5-Cyclopropyl-6-(1,1,1-trifluoropropan-2-yloxy)picolinic acid

HRID 624863

반응식

HRID 624863 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([C:15]([OH:17])=[O:16])=[N:6][C:7]=1[O:8][CH:9]([CH3:14])[C:10]([F:13])([F:12])[F:11].[CH:18]1([B-](F)(F)F)[CH2:20][CH2:19]1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(PC12CC3CC(CC(C3)C1)C2)CCC>[CH:18]1([C:2]2[CH:3]=[CH:4][C:5]([C:15]([OH:17])=[O:16])=[N:6][C:7]=2[O:8][CH:9]([CH3:14])[C:10]([F:13])([F:12])[F:11])[CH2:20][CH2:19]1

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 23697338Potassium cyclopropyltrifluoroborateHCID 710875825-Bromo-6-(1,1,1-trifluoropropan-2-yloxy)picolinic acid

생성물 1

HCID 710874355-Cyclopropyl-6-(1,1,1-trifluoropropan-2-yloxy)picolinic acid수율 79%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 68995490Butyl-1-adamantylphosphine촉매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

5-Bromo-6-(1,1,1-trifluoropropan-2-yloxy)picolinic acid (2 g, 6.37 mmol), potassium cyclopropyltrifluoroborate (952 mg, 6.43 mmol), cesium carbonate (6.22 g, 19.1 mmol) and palladium(II)acetate (28.6 mg, 127 μmol) were suspended in toluene (55 mL) and water (6.11 mL) under an argon atmosphere. Butyl-1-adamantylphosphin (68.5 mg, 191 μmol) was added, the reaction mixture was heated to 120° C. for 1 d, poured onto ice-water/1N HCl (150 mL) and extracted with EtOAc (2×300 mL). The combined organic layers were washed with ice-water/brine (150 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (1.38 g, 79%) as a yellow solid. MS (EI): m/e=276.2 [M+H]+.

후처리

  1. additionpoured onto ice-water/1N HCl (150 mL)
  2. extractionextracted with EtOAc (2×300 mL)
  3. washThe combined organic layers were washed with ice-water/brine (150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f8f51eff5cd34051872e2767fc006127
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303012B2

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