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

HRID 624863

反応式

HRID 624863 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 68995490Butyl-1-adamantylphosphine触媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-f8f51eff5cd34051872e2767fc006127
出典データセット
uspto-grants-2016_04
特許番号
US09303012B2

関連ノート

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