Potassium Carbonate → Methyl 3-[5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 327243Notes

Reaction equation

HRID 327243 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:5]2.Br[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[CH2:20][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124174182-(Bromomethyl)quinolineHCID 18947616Methyl 3-[5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Product 1

HCID 18947552Methyl 3-[5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoateYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the phenol from step B (13.62 g, 55.14 mmol) and 2-bromomethylquinoline (12.85 g, 1.05 mol eq.) and anhydrous K2CO3 (15.22 g, 2 mol. eq.) in DMF (40 ml) was stirred at RT for 48 hours. The mixture was then poured onto ice/water and after all the ice had melted, the brown solid was collected and air-dried. The dried material was passed through a plug of silica (using EtOAc/hexane (1:3) as eluent) to remove the color; yield: 19 g, 88%. Recrystallization from EtOH afforded 14.17g of pure title compound, m.p. 131°-132° C.

Workup

  1. additionThe mixture was then poured onto ice/water
  2. customthe brown solid was collected
  3. customair-dried
  4. customto remove the color
  5. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-a754ea329bed47ff9f6be633c78dfe3e
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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