Potassium Carbonate → Methyl 3-[N-methyl-3-(p-chlorobenzoyl)-6-(quinolin-2-ylmethoxy)indol-2-yl]2,2-dimethylpropanoate

HRID 1590729Notes

Reaction equation

HRID 1590729 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[C:4]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:3]1[CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+].Br[CH2:36][C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=1>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:36][C:37]3[CH:46]=[CH:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=3)[CH:9]=2)[C:4]([C:12](=[O:20])[C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:3]1[CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124174182-(Bromomethyl)quinolineHCID 18947581Methyl 3-[N-methyl-3-(p-chlorobenzoyl)-6-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Product 1

HCID 18947635Methyl 3-[N-methyl-3-(p-chlorobenzoyl)-6-(quinolin-2-ylmethoxy)indol-2-yl]2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 180 mg of the phenol from Step E in 5 mL of DMF were added 124 mg of milled K2CO3 followed by 150 mg of 2-(bromomethyl) quinoline. The mixture was stirred at R.T. for 18 h, poured onto 25% aq. NH4OAc and extracted with ethyl acetate. The extract was dried over Na2SO4 and evaporated to dryness to give an oil which was chromatographed on flash silica gel using ethyl acetate:hexane (30:70) as eluant to give the title compound as a foam.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over Na2SO4
  3. customevaporated to dryness
  4. customto give an oil which
  5. customwas chromatographed on flash silica gel

Sources & evidence

ORD record
ord-af7ab0fd95fd45f0801574667aeaaac8
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

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