Sodium Hydroxide → HCID 178430493, compound

HRID 593904Notes

Reaction equation

HRID 593904 reaction equation
[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[NH:17][N:16]=[N:15][N:14]=3)[CH:9]=[C:8]([C:18]([O:20]C)=[O:19])[C:7]=2[C:6]([CH3:22])=[CH:5]1)([CH3:3])[CH3:2].[OH-].[Na+]>CO.O1CCCC1>[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[NH:17][N:16]=[N:15][N:14]=3)[CH:9]=[C:8]([C:18]([OH:20])=[O:19])[C:7]=2[C:6]([CH3:22])=[CH:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178497408HCID 178497408, compound

Product 1

HCID 178430493HCID 178430493, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 1-isopropyl-3-methyl-6-(1H-tetrazol-5-yl)-1H-indole-4-carboxylate (0.27 g, 0.902 mmol) in MeOH (15 mL) and tetrahydrofuran (5 mL) was added 1N NaOH (5 mL, 5.00 mmol). The reaction was heated to 60° C. and stirred for 48 hr. LCMS showed that the reaction was complete. The reaction was concentrated to near dryness under vacuum, acidified with 1N HCl (5 mL), triturated, filtered and washed with a small volume of water, and dried under vacuum to give the product 1-isopropyl-3-methyl-6-(1H-tetrazol-5-yl)-1H-indole-4-carboxylic acid (0.26 g, 0.911 mmol, 101% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 13.04 (br. s., 1H), 8.36 (d, J=1.5 Hz, 1H), 8.13 (d, J=1.3 Hz, 1H), 7.65 (s, 1H), 4.85 (quin, J=6.6 Hz, 1H), 2.36 (s, 3H), 1.50 (d, J=6.6 Hz, 6H). MS(ES)+ m/e 286.1 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customtriturated
  3. filtrationfiltered
  4. washwashed with a small volume of water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-22d143f26a234d0ca802699d86beccb9
Source dataset
uspto-grants-2016_01
Patent number
US09242962B2

Reaction notes

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