Hydrochloric Acid → HCID 67814566, compound

HRID 1616813Notes

Reaction equation

HRID 1616813 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[C:8]([C:17]([O:19]C)=[O:18])[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=2)[N:6]([CH3:21])[CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1.CO>[CH:1]([C:4]1[C:12]2[C:7](=[C:8]([C:17]([OH:19])=[O:18])[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=2)[N:6]([CH3:21])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67814189HCID 67814189, compound

Product 1

HCID 67814566HCID 67814566, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 3-isopropyl-1-methyl-5-(methylsulfonyl)-1H-indole-7-carboxylate (500 mg, 1.61 mmol) in THF/MeOH (3:1 mL) was treated with 5N NaOH (3 mL). The yellow biphasic solution was stirred at room temperature under nitrogen overnight. 6N HCl was added to pH 4 and the solution was stirred at room temperature for 2 hours. Solids were filtered and dried in vacuum-oven for 3 hours to give 3-isopropyl-1-methyl-5-(methylsulfonyl)-1H-indole-7-carboxylic acid (167 mg, 35%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.39 (d, J=6.8 Hz, 6H) 3.15 (s, 3H) 3.27 (quin, J=6.82 Hz, 1H) 3.95-4.02 (m, 3H) 7.03 (s, 1H) 8.40 (d, J=2.02 Hz, 1H) 8.45 (d, J=1.77 Hz, 1H) MS (ES). [M+H]+ 296.2.

Workup

  1. stirringthe solution was stirred at room temperature for 2 hours
  2. filtrationSolids were filtered
  3. customdried in vacuum-oven for 3 hours

Sources & evidence

ORD record
ord-4fa050afb1ba46e7a9bad831f8bf1a1e
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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