Sodium Bicarbonate → HCID 73057752、化合物

HRID 2207329ノート

反応式

HRID 2207329 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:18])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[N:13][CH:12]=3)=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.C(=O)([O-])O.[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:19][N:20]1[CH:24]=[C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:9][C:10](=[O:18])[C:11]4[C:16]([CH:17]=3)=[CH:15][CH:14]=[N:13][CH:12]=4)=[CH:4][CH:3]=2)[CH:22]=[N:21]1

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 90040060HCID 90040060、化合物

生成物 1

HCID 73057752HCID 73057752、化合物

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

A suspension of 3-(4-bromo-phenyl)-2H-[2,7]naphthyridin-1-one (63.2 mg, 0.210 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (65.5 mg, 0.32 mmol) and sodium hydrogen carbonate (21.2 mg, 0.25 mmol) in DMF (1 ml) and water (0.25 ml) is flushed with nitrogen and heated to 40° C. Then bis(triphenylphosphine)-palladium(II)-chloride (3.0 mg, 0.004 mmol) is added. The reaction mixture is heated to 80° C. and stirred at this temperature for 20 hours. The mixture is allowed to cool to room temperature and excess water is added. The resulting precipitate is filtered off washed with water and dried under vacuum to afford 3-[4-(1-methyl-1H-pyrazol-4-yl)-phenyl]-2H-[2,7]naphthyridin-1-one as olive green solid; HPLC/MS 1.33 min (A), [M+H] 303;

後処理

  1. customis flushed with nitrogen
  2. temperatureThe reaction mixture is heated to 80° C.
  3. temperatureto cool to room temperature
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with water
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-a161fbb6afd6410b95c04c99a7c2c691
出典データセット
uspto-grants-2016_06
特許番号
US09376433B2

反応ノート

読み込み中…