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

HRID 2359407노트

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HRID 2359407 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fdda792a98ee4617a9e93bf47d884ed2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685970B2

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