Dichloromethane → 2-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acid

HRID 2359435

反応式

HRID 2359435 の反応式
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[N:20][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>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]>[CH3:15][C:16]1[CH:17]=[C:18]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:19]=[N:20][CH:21]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27627085-Methylpyridine-3-boronic acidHCID 190262012-Chloroquinoline-8-carboxylic acid

生成物 1

HCID 581546112-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acid収率 72.1%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
125 °C

実験手順

A mixture of 2-chloroquinoline-8-carboxylic acid (0.600 g, 2.8 mmol), 5-methylpyridin-3-ylboronic acid (0.410 g, 3.0 mmol), K3PO4 (1.1 g, 5.2 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.10 g, 0.122 mmol) in DMF (3 mL) and water (1 mL) was microwave heated (125° C.×1 Hour). The mixture was filtered over celite and the celite cake was washed with ethyl acetate (30 mL). The filtrate was combined with 60 mL aqueous saturated NaHCO3 solution and the mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane) to obtain 2-(5-methylpyridin-3-yl)quinoline-8-carboxylic acid (0.535 g, 2.02 mmol).

後処理

  1. filtrationThe mixture was filtered over celite
  2. washthe celite cake was washed with ethyl acetate (30 mL)
  3. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane)

出典と根拠

ORDレコード
ord-f9bb6a143c27405c83db57eab064cfba
出典データセット
uspto-grants-2014_04
特許番号
US08685970B2

関連ノート

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