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Quinoline → 6-Isopropyl-8-[3-(hydroxymethyl)phenyl]quinoline

HRID 857271
노트
인쇄 미리보기

반응식

HRID 857271 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH:11][CH2:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.[C:22]([O-])([O-])=O.[Na+].[Na+].CO[CH2:30][CH2:31]OC>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:30]([C:7]1[CH:6]=[C:5]2[C:10](=[C:9]([C:17]3[CH:18]=[C:13]([CH2:12][OH:11])[CH:14]=[CH:15][CH:16]=3)[CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)([CH3:31])[CH3:22]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7047QuinolineHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

생성물 1

HCID 218656306-Isopropyl-8-[3-(hydroxymethyl)phenyl]quinoline

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of Quinoline 1 (1.0 eq), 3-(hydroxymethyl)phenylboronic acid (1.3 eq), aqueous Na2CO3 (2.0M; 3.2 eq) and Pd(PPh3)4 (0.048 eq) in DME (0.15M) was stirred at 80° C. for 12 h. The resulting mixture was cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 1:1) and stirring in Et2O yielded the title compound as a white solid after filtration.

후처리

  1. temperatureThe resulting mixture was cooled to room temperature
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringFlash chromatography (Hex:EtOAc; 1:1) and stirring in Et2O

출처 및 근거

ORD 기록
ord-979b390299564e7896a45b03fc838cb1
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07144896B2

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