Potassium Carbonate → HCID 19737269, compound

HRID 258475Notes

Reaction equation

HRID 258475 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1)[OH:13])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][C:33]([Cl:39])=[CH:34][CH:35]=2)[N:30]=1>CC(C)=O>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][C:33]([Cl:39])=[CH:34][CH:35]=3)[N:30]=2)[CH:15]=1)[OH:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 102441602-(Bromomethyl)-7-chloroquinolineHCID 19737286HCID 19737286, compound

Product 1

HCID 19737269HCID 19737269, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the phenol of Step 4 (3.322 g, 12.3 mmol), K2CO3 (4.08 g, 29.5 mmol) and 2-(bromomethyl)-7-chloroquinoline (3.771 g, 14.7 mmol) in 60 mL of acetone was heated to reflux for 8 h. CD2Cl2 (100 mL) was added and the mixture was filtered through silica with EtOAc. Flash chromatography of the residue on silica using EtOAc:toluene 15:85 and 20:80 afforded 5.145 g (94%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. additionCD2Cl2 (100 mL) was added
  4. filtrationthe mixture was filtered through silica with EtOAc

Sources & evidence

ORD record
ord-856beb7c00774745a2b65112fc2d6068
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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