Dimethylformamide → Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate

HRID 628850ノート

反応式

HRID 628850 の反応式
Cl[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].CN(C=O)C>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]>[CH3:14][O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:22]1[CH:23]=[CH:24][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:20][CH:21]=1)[C:11]([CH3:12])=[CH:10]2

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 27343694-Methoxycarbonylphenylboronic acidHCID 49146642-Chloro-6-methoxy-3-methylquinoline

生成物 1

HCID 66980055Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate収率 25%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(methoxycarbonyl)phenylboronic acid (184 mg, 1.02 mmol), TEA (0.35 mL, 2.41 mmol), and PdCl2(dppf) (35 mg, 0.048 mmol) was added 2 mL of DMF under argon. The mixture was then stirred for 2.5 h at 120° C. in a microwave reactor. The crude mixture was then diluted with water (25 mL) and extracted with EtOAc (25 mL×2). The organics were washed with brine (50 mL), dried over sodium sulfate, and concentrated to yield 250 mg of crude material. The crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes to yield 37 mg (25% yield) of methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate.

後処理

  1. extractionextracted with EtOAc (25 mL×2)
  2. washThe organics were washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto yield 250 mg of crude material
  6. customThe crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes

出典と根拠

ORDレコード
ord-972b8b97ff7b4039b1d08ea32c45a9ac
出典データセット
uspto-grants-2016_04
特許番号
US09315462B2

反応ノート

読み込み中…