1,2-Dimethoxyethane → 2'-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

HRID 2091819ノート

反応式

HRID 2091819 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[F:19])[CH:8]=[C:9](I)[CH:10]=1)=[O:4].[CH:20]([N:23]1[C:27](B(O)O)=[CH:26][CH:25]=[N:24]1)([CH3:22])[CH3:21].CC([O-])=O.[K+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[F:19])[CH:8]=[C:9]([C:27]2[N:23]([CH:20]([CH3:22])[CH3:21])[N:24]=[CH:25][CH:26]=2)[CH:10]=1)=[O:4]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 517044Potassium AcetateHCID 23139440(1-Isopropyl-1H-pyrazol-5-yl)boronic acidHCID 594325542'-Fluoro-5-iodo-4'-methyl-biphenyl-3-carboxylic acid methyl ester

生成物 1

HCID 577706482'-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester収率 55.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

To a microwave vessel was added 2′-fluoro-5-iodo-4′-methyl-biphenyl-3-carboxylic acid methyl ester (1.91 g, 5.4 mmol), 2-isopropyl-2H-pyrazole-3-boronic acid (1.08 g, 7.02 mmol), KOAc (1.59 g, 16.2 mmol), Pd(PPh3)4 (0.187 g, 0.16 mmol), dimethylglycol (15 mL) and water (3 mL). The mixture was flushed with N2 before submitting to microwave heating at 130° C. for 1 hour. After cooling down to room temperature, the reaction mixture was extracted with EtOAc and the combined organic layers were washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column to afford 2′-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester as a viscous oil (1.0 g, 55.2%).

後処理

  1. customThe mixture was flushed with N2
  2. temperatureAfter cooling down to room temperature
  3. extractionthe reaction mixture was extracted with EtOAc
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column

出典と根拠

ORDレコード
ord-f1f047b38d5a4230abcccf13a89d554b
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…