Dichloromethane → 2-(3-(Difluoromethyl)phenyl)quinoline-8-carboxylic acid

HRID 2359407ノート

反応式

HRID 2359407 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.[F:15][CH:16]([F:32])[C:17]1[CH:18]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:20]=[CH:21][CH:22]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>COCCOC.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]>[F:15][CH:16]([F:32])[C:17]1[CH:22]=[C:21]([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:20]=[CH:19][CH:18]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 190262012-Chloroquinoline-8-carboxylic acidHCID 222401672-(3-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 581546842-(3-(Difluoromethyl)phenyl)quinoline-8-carboxylic acid収率 80.2%

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2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

To a solution of 2-chloroquinoline-8-carboxylic acid (3.1 g, 15.0 mmol) in DME (20 mL) and water (2 mL) was added 2-(3-(difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.5 g, 17.7 mmol), K3PO4 (5.2 g, 22.6 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.50 g, 0.63 mmol). The reaction mixture was stirred under nitrogen at 85° C. for 12 hours, then the reaction was cooled to room temperature and water (20 mL) was added. The mixture was filtered and the filter cake was washed with water, and the solid was dried in vacuo to give 2-(3-(difluoromethyl)phenyl)quinoline-8-carboxylic acid (3.6 g, 80% yield).

後処理

  1. temperaturethe reaction was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. washthe filter cake was washed with water
  4. customthe solid was dried in vacuo

出典と根拠

ORDレコード
ord-fdda792a98ee4617a9e93bf47d884ed2
出典データセット
uspto-grants-2014_04
特許番号
US08685970B2

反応ノート

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