Potassium Hydroxide → HCID 59200046, compound

HRID 2382051Notes

Reaction equation

HRID 2382051 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[N:7]([NH:15][C:16]([C:18]2[C:19]([CH3:30])=[N:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:22][CH:23]=2)=[O:17])[CH:6]=1)=[O:4].[OH-].[K+]>CO.O.CCOC(C)=O>[F:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH:15][C:16]([C:18]1[C:19]([CH3:30])=[N:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:22][CH:23]=1)=[O:17])[CH:6]=[C:5]2[C:3]([OH:4])=[O:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 68557157HCID 68557157, compound

Product 1

HCID 59200046HCID 59200046, compoundYield 19.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-fluoro-1-[(4-methyl-2-pyridin-2-yl-pyrimidine-5-carbonyl)-amino]-1H-indole-3-carboxylic acid methyl ester (2.6 mmol) in MeOH (10 mL) is treated with an aqueous solution of KOH (500 mg, 8.9 mmol) in H2O (200 mL) and heated at reflux for 2 h. The mixture is diluted with EtOAc (50 mL) and extracted with 1% aqueous KOH (3×50 mL). The combined aqueous layer is neutralized with HCl (conc.), and the precipitate is collected by filtration and dried in vacuo to afford 5-fluoro-1-[(4-methyl-2-pyridin-2-yl-pyrimidine-5-carbonyl)-amino]-1H-indole-3-carboxylic acid (195 mg, 19%, 3 steps). MS: 392 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 12.44 (s, OH, 1H), 12.31 (s, NH, 1H), 9.31 (s, 1H), 8.81 (d, 1H), 8.48 (d, 1H), 8.35 (s, 1H), 8.03 (m, 1H), 7.77 (m, 1H), 7.62 (m, 2H), 7.19 (m, 1H), 2.79 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. extractionextracted with 1% aqueous KOH (3×50 mL)
  4. filtrationthe precipitate is collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dc89bc06e76f49a3af8fb8acac68d771
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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