Sodium Carbonate → HCID 21865637, compound

HRID 896651Notes

Reaction equation

HRID 896651 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([S:15]([CH3:18])(=[O:17])=[O:16])([CH3:14])[CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[OH:19][CH2:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:18][S:15]([C:12]([C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([C:25]3[CH:26]=[C:21]([CH2:20][OH:19])[CH:22]=[CH:23][CH:24]=3)[CH:3]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:14])[CH3:13])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 111632478-Bromo-6-[2-(methanesulfonyl)propan-2-yl]quinoline

Product 1

HCID 21865637HCID 21865637, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of the 8-Bromo-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline from Step 2 above (26 g, 79 mmol), 3-(hydroxymethyl)phenyl-boronic acid (14 g, 92 mmol), sodium carbonate (120 mL, 2M, H2O), PdCl2(Ph3P)2 (2 g) in DME (300 mL) was heated at 90-100° C. for 8 h. The resulting reaction mixture was filtered on a large plug/column of silica gel and the eluted with EtOAc. The organic extracts were concentrated and the resulting suspension diluted with Et2O and stirred vigorously for 3 h. The desired {3-[6-(1-Methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-methanol was isolated as a white solid by filtration.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered on a large plug/column of silica gel
  3. washthe eluted with EtOAc
  4. concentrationThe organic extracts were concentrated
  5. additionthe resulting suspension diluted with Et2O

Sources & evidence

ORD record
ord-2dda1f7930d64e8b9b1eacb85d4bc50b
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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