HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 857271
Notes
Print preview

Reaction equation

HRID 857271 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-979b390299564e7896a45b03fc838cb1
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07144896B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes