Ethyl 4-chloroquinazoline-2-carboxylate → (4-Chloroquinazolin-2-yl)(3-fluorophenyl)methanone

HRID 625731ノート

反応式

HRID 625731 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14]CC)=O)[N:3]=1.[F:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][CH:23]=1>C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([F:17])[CH:23]=2)=[O:14])[N:3]=1

参加物

4

反応物 2

HCID 3477840Ethyl 4-chloroquinazoline-2-carboxylateHCID 178505773HCID 178505773、化合物

生成物 1

HCID 86649047(4-Chloroquinazolin-2-yl)(3-fluorophenyl)methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

To a suspension of ethyl 4-chloroquinazoline-2-carboxylate (237 mg, 1 mmol) in THF (5 mL) was added dropwise a 1M solution of 3-fluorophenylmagnesium bromide in THF (2 mL, 2 mmol) at −20° C. The reaction mixture was stirred at −20° C. for 4 h. The mixture was quenched by adding 0.5 N HCl solution (5 mL) and the biphasic mixture was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine and dried over MgSO4. (4-chloroquinazolin-2-yl)(3-fluorophenyl)methanone was obtained as a yellow solid (190 mg, 66%). LC-MS (ESI) m/z 287 (M+H)+.

後処理

  1. customThe mixture was quenched
  2. additionby adding 0.5 N HCl solution (5 mL)
  3. extractionthe biphasic mixture was extracted with EtOAc (2×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-c9adf62b5e1e438681ce96cc49ff8919
出典データセット
uspto-grants-2016_04
特許番号
US09308207B2

反応ノート

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