Potassium Phosphate, Tribasic → 5-Cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

HRID 632183노트

반응식

HRID 632183 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](Br)=[C:7]([O:12][CH2:13][CH2:14][O:15][CH3:16])[N:6]=1)=[O:4].[CH:17]1(B(O)O)[CH2:19][CH2:18]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:17]2[CH2:19][CH2:18]2)=[C:7]([O:12][CH2:13][CH2:14][O:15][CH3:16])[N:6]=1)=[O:4]

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 710877995-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

생성물 1

HCID 710874485-Cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester수율 142.9%

시약·촉매·용매 4

HCID 75806Tricyclohexylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

Under an atmosphere of nitrogen, a solution of 5-bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester (0.2 g, 0.7 mmol), cyclopropylboronic acid (CAN 411235-57-9, 81 mg, 0.9 mmol), palladium acetate (CAN 3375-31-3, 8 mg, 0.037 mmol), tricyclohexylphosphine (CAN 2622-14-2, 0.021 g, 0.07 mmol) and potassium phosphate (0.54 g, 0.20 mmol) in toluene (20 mL) and water (1 mL) was heated to 110° C. for 48 h. The reaction mixture was concentrated under reduced pressure, dissolved in water, extracted with ethyl acetate (3×30 mL), washed with brine, dried (sodium sulfate) and evaporated to dryness. The residue was purified by column chromatography (silica gel, 10 g, 5% ethyl acetate in petroleum ether) to yield the title compound (0.16 g, 1 mmol, 93%) as yellow oil; MS (EI): m/e 252.2 [M+H]+.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography (silica gel, 10 g, 5% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-3cb1026b972142148cbd28e982fe72db
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321727B2

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