Cesium carbonate → 2-Chloro-6-(3,5-dimethoxyphenyl)-8-fluoroquinazoline

HRID 2404063ノート

反応式

HRID 2404063 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[C:7]([Cl:13])[N:6]=[CH:5]2.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:13][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[C:10]([F:12])[CH:11]=[C:2]([C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=3)[CH:3]=2)[N:8]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 591992866-Bromo-2-chloro-8-fluoroquinazoline

生成物 1

HCID 867135972-Chloro-6-(3,5-dimethoxyphenyl)-8-fluoroquinazoline収率 51%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-bromo-2-chloro-8-fluoroquinazoline (4.0 g, 15.4 mmol), 3,5-dimethoxyphenylboronic acid (4.47 g, 16.9 mmol), cesium carbonate (10.0 g, 30.8 mmol) and Pd(PPh3)2Cl2 (236 mg, 0.77 mmol) in THF (200 mL) and water (10 mL) was degassed with nitrogen three times, and stirred at 80° C. for 3 h. Both TLC and LCMS showed the reaction was completed. The reaction mixture was cooled to RT and directly concentrated. The residue was purified by silica gel chromatography (petroleum ether:dichloromethane=2:1 to 1:1) to afford the title compound (2.5 g, 51%) as a yellow solid. MS (ES+) C16H12ClFN2O2 requires: 318/320. found: 319/321 [M+H]+.

後処理

  1. customwas degassed with nitrogen three times
  2. temperatureThe reaction mixture was cooled to RT
  3. concentrationdirectly concentrated
  4. customThe residue was purified by silica gel chromatography (petroleum ether:dichloromethane=2:1 to 1:1)

出典と根拠

ORDレコード
ord-d55d2520771849fca3ed092602593d1e
出典データセット
uspto-grants-2014_08
特許番号
US08802697B2

反応ノート

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