Sodium Hydroxide → HCID 67467437, compound

HRID 42514Notes

Reaction equation

HRID 42514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:15]([O:17]CC)=[O:16])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]3[CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[OH-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]3[CH2:12][CH2:13][CH2:14]3)[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67467592ethyl 6-bromo-1-cyclobutyl-1H-indole-4-carboxylate

Product 1

HCID 67467437HCID 67467437, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-bromo-1-cyclobutyl-1H-indole-4-carboxylate (0.3 g, 0.973 mmol) (crude residue from above) in MeOH (8 mL) and THF (2 mL) was added 3 M NaOH (1.298 mL, 3.89 mmol). The reaction was stirred at RT for 16 h, at which time the volatiles were removed in vacuo. The residue was diluted with water and slowly acidifed with 1 N HCl to pH 3-4. The solids were filtered and dried on hivac for 16 h to give 6-bromo-1-cyclobutyl-1H-indole-4-carboxylic acid (0.21 g, 0.535 mmol, 55.0% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.79-1.89 (m, 2H) 2.34-2.46 (m, 2H) 3.84 (s, 1H) 5.08 (t, J=8.21 Hz, 1H) 6.99 (d, J=3.03 Hz, 1H) 7.75-7.79 (m, 1H) 7.81 (d, J=3.03 Hz, 1H) 8.01-8.05 (m, 1H) 13.03 (br. s., 1H). MS (ES) [M+H]+ 294.1.

Workup

  1. customwere removed in vacuo
  2. additionThe residue was diluted with water
  3. filtrationThe solids were filtered
  4. customdried on hivac for 16 h

Sources & evidence

ORD record
ord-f2548f9d0d4449e195baff94512be4a9
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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