Sodium Hydroxide → 4-(2-Fluorophenyl)-7-methyl-6-(pyrimidin-5-yloxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361254Notes

Reaction equation

HRID 2361254 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([CH3:28])=[C:17]([O:21][C:22]4[CH:23]=[N:24][CH:25]=[N:26][CH:27]=4)[CH:18]=3)[NH:13][C:12]=2[C:11]([C:29]([O:31]CC)=[O:30])=[N:10][CH:9]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([CH3:28])=[C:17]([O:21][C:22]4[CH:27]=[N:26][CH:25]=[N:24][CH:23]=4)[CH:18]=3)[NH:13][C:12]=2[C:11]([C:29]([OH:31])=[O:30])=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67994650Ethyl 4-(2-fluorophenyl)-7-methyl-6-(pyrimidin-5-yloxy)-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679951684-(2-Fluorophenyl)-7-methyl-6-(pyrimidin-5-yloxy)-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 4-(2-fluorophenyl)-7-methyl-6-(pyrimidin-5-yloxy)-9H-pyrido[3,4-b]indole-1-carboxylate (0.08 g, 0.181 mmol) and 1N aqueous NaOH (0.814 mL, 0.814 mmol) in methanol (3.01 mL) was refluxed. After 1 hr, the reaction was cooled to room temperature and concentrated in vacuo. Water was added, and the solution was acidified to pH ˜4 by litmus paper. The precipitate was filtered, washed with water, and dried over Drierite to give the desired product (0.0456 g, 0.110 mmol, 60.9% yield) as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater was added
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. dry with materialdried over Drierite

Sources & evidence

ORD record
ord-05586ab953a147a4ac771496f1fa699c
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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