Sodium Carbonate → Methyl 4-(6-methoxyquinolin-2-yl)benzoate

HRID 55819

反応式

HRID 55819 の反応式
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:21]1[CH:22]=[CH:23][C:18]([C:16]([O:15][CH3:14])=[O:17])=[CH:19][CH:20]=1)[CH:11]=[CH:10]2

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 836472-Chloro-6-methoxyquinolineHCID 27343694-Methoxycarbonylphenylboronic acid

生成物 1

HCID 66980098Methyl 4-(6-methoxyquinolin-2-yl)benzoate

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-chloro-6-methoxyquinoline (see U.S. 61/391,225 for synthesis) (200 mg, 1.0 mmol), 4-(methoxycarbonyl) phenylboronic acid (205 mg, 1.1 mmol), Pd(dppf)Cl2 (366 mg, 0.5 mmol) and sodium carbonate (212 mg, 2.0 mmol) in 1,4-dioxane/water (3 mL/0.6 mL) was heated to 120° C. by microwave for 1 h. The precipitates were filtered; washed with EtOAc (10 mL), acetone (10 mL) and water (10 mL) separately; dried to give the product as a black solid. (120 mg, 40.9%).

後処理

  1. filtrationThe precipitates were filtered
  2. washwashed with EtOAc (10 mL), acetone (10 mL) and water (10 mL) separately
  3. customdried

出典と根拠

ORDレコード
ord-0c6c5bb0a5c943cab6c7cb134fb85ce2
出典データセット
uspto-grants-2016_09
特許番号
US09433618B2

関連ノート

読み込み中…