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

HRID 857271Notes

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]

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 178418397HCID 178418397, compoundCatalystHCID 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
Patent number
US07144896B2

Reaction notes

Loading…