1,2-Dimethoxyethane → HCID 57770606, 화합물

HRID 2091822노트

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HRID 2091822 반응식
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6](Br)[CH:5]=1.COCCOC.[CH:25]1([CH2:28][N:29]2[C:33](B(O)O)=[CH:32][CH:31]=[N:30]2)[CH2:27][CH2:26]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([C:33]2[N:29]([CH2:28][CH:25]3[CH2:27][CH2:26]3)[N:30]=[CH:31][CH:32]=2)[CH:5]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 57770642HCID 57770642, 화합물HCID 59599704Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

생성물 1

HCID 57770606HCID 57770606, 화합물수율 100.3%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

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온도
60 °C

실험 절차

3-Bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (1.0 g, 3.27 mmol) and palladium tetrakis(triphenylphosphine) (0.189 g, 0.164 mmol) were added to 25 mL DME, and the mixture was stirred at 60° C. for 10 minutes. 1-Cyclopropylmethyl-1H-pyrazole-5-boronic acid (0.65 g, 3.92 mmol) was added, followed by a solution of K3PO4 (1.39 g, 6.54 mmol) in 5 mL water. The mixture was refluxed for six hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (3:1 EtOAc/hexanes) to give 1.14 g of 3-(2-cyclopropylmethyl-2H-pyrazol-3-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=348.

후처리

  1. temperatureThe mixture was refluxed for six hours
  2. temperaturecooled to room temperature
  3. custompartitioned between water and EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via flash chromatography (3:1 EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-f37d830bb28b473bb88904008b07134d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440673B2

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