1,2-Dimethoxyethane → HCID 57770606、化合物

HRID 2091822ノート

反応式

HRID 2091822 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 57770606HCID 57770606、化合物収率 100.3%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f37d830bb28b473bb88904008b07134d
出典データセット
uspto-grants-2013_05
特許番号
US08440673B2

反応ノート

読み込み中…