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

HRID 632452

反応式

HRID 632452 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+].Cl>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(PC12CC3CC(CC(C3)C1)C2)CCC.O>[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

9

反応物 4

HCID 313Hydrochloric AcidHCID 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 4

HCID 167845palladium(II) acetate触媒HCID 68995490Butyl-1-adamantylphosphine触媒HCID 962Water溶媒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 icewater/1N HCl (150 mL) and extracted with EtOAc (2×300 mL). The combined organic layers were washed with icewater/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. extractionextracted with EtOAc (2×300 mL)
  2. washThe combined organic layers were washed with icewater/brine (150 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ae0dddf6dcb44928a58fb06af65a7bda
出典データセット
uspto-grants-2016_04
特許番号
US09321727B2

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