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

HRID 56473ノート

反応式

HRID 56473 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 hours. The reaction mixture was cooled to room temperature 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 room temperature
  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-11ee6a2662df4733b3d66f32f632f1c1
出典データセット
uspto-grants-2016_09
特許番号
US09434700B2

反応ノート

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