Cerous carbonate → 2-Chloro-6-(3,5-dimethoxyphenyl)-7-methoxyquinazoline

HRID 524075

反応式

HRID 524075 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([Cl:14])[N:6]=[CH:5]2.[CH3:15][O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1.C(=O)([O-])[O-].[Ce+3].C(=O)([O-])[O-].C(=O)([O-])[O-].[Ce+3]>C1COCC1.O1CCOCC1.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:14][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:2]([C:19]3[CH:18]=[C:17]([O:16][CH3:15])[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=3)[CH:3]=2)[N:8]=1

参加物

8

反応物 3

HCID 160516Cerous carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 591992766-Bromo-2-chloro-7-methoxyquinazoline

生成物 1

HCID 867135952-Chloro-6-(3,5-dimethoxyphenyl)-7-methoxyquinazoline収率 38%

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

A mixture of 6-bromo-2-chloro-7-methoxyquinazoline (2.4 g, 8.82 mmol), 3,5-dimethoxyphenylboronic acid (1.6 g, 8.82 mmol), cerium carbonate (8.6 g, 26.46 mmol) and Pd(PPh3)2Cl2 (1.4 g, 2.1 mmol) in THF (10 mL), dioxane (10 mL) and water (2 mL) was degassed with nitrogen three times and stirred at 85° C. for 3 h. LCMS monitored the reaction was completed. The mixture was cooled to RT and extracted with dichloromethane (3×50 mL). The organic layers were separated, combined, washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether: ethyl acetate=1:4) to give the title compound (1.1 g, 38%) as a white solid. MS (ES+) C17H15ClN2O3 requires: 330, 332. found: 331, 333 [M+H]+.

後処理

  1. customwas degassed with nitrogen three times
  2. temperatureThe mixture was cooled to RT
  3. extractionextracted with dichloromethane (3×50 mL)
  4. customThe organic layers were separated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (petroleum ether: ethyl acetate=1:4)

出典と根拠

ORDレコード
ord-493b48ac62424dde8422c62e63ea89be
出典データセット
uspto-grants-2016_05
特許番号
US09340514B2

関連ノート

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