Sodium Hydroxide → 1-Methyl-5-[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxamido]-1h-indole-2-carboxylic acid sodium salt hydrate

HRID 489998Notes

Reaction equation

HRID 489998 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:30]([O:32]CC)=[O:31].[OH-].[Na+:36]>C(O)C>[OH2:13].[Na+:36].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:30]([O-:32])=[O:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262720Ethyl 1-methyl-5-{[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carbonyl]amino}-1H-indole-2-carboxylate

Product 1

HCID 1317244131-Methyl-5-[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxamido]-1h-indole-2-carboxylic acid sodium salt hydrateYield 151.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-methyl-5-[4′-(trifluoromethyl)[1,1′-biphenyl]-2-carboxamido]-1H-indole-2-carboxylate (46.7 g) from the previous step and aqueous sodium hydroxide (8.0 g in 140 ml) were combined in refluxing ethanol (280 mL) for 1 hour. The solution was cooled, granulating overnight and the resulting slurry was filtered. The product solids were washed with an ethanol-water mixture and dried, yielding the title compound, 1-methyl-5-[4′-(trifluoromethyl)[1,1′-biphenyl]-2-carboxamido]-1H-indole-2-carboxylic acid sodium salt hydrate (36.3 g, 79% as-is). Anhydrous Mol wt of parent acid (calc) 438.41, MS: 439.2 (MH+), 437.0 (M−). 1H NMR (DMSO-d6): δ 4.00 (s, 3H), 6.55 (s, 1H), 7.12-7.75 (complex, 11H), 10.04 (s, 1H).; HPLC retention time 9.30 minutes.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe resulting slurry was filtered
  3. washThe product solids were washed with an ethanol-water mixture
  4. customdried

Sources & evidence

ORD record
ord-38d0cee025684327ae6b2ec31ff3d9a7
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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