Sodium Hydroxide → 6-bromo-1-cyclopropyl-1H-indole-4-carboxylic acid

HRID 516770

Reaction equation

HRID 516770 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([O:16]C)=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]3[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:14]([OH:16])=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]3[CH2:13][CH2:12]3)[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67467490methyl 6-bromo-1-cyclopropyl-1H-indole-4-carboxylate

Product 1

HCID 674651346-bromo-1-cyclopropyl-1H-indole-4-carboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-bromo-1-cyclopropyl-1H-indole-4-carboxylate (0.43 g, 1.462 mmol) in MeOH (12 mL) and THF (3 mL) was added 3 M NaOH (1.949 mL, 5.85 mmol). The reaction was stirred for 18 h at RT, at which time the volatiles were removed in vacuo. The residue was diluted with water and slowly acidified with 1 N HCl to pH 4-5, then extracted with EtOAc (2x). The combine organics were wash with brine, dried over magnesium sulfate, filtered, and concentrated to give 6-bromo-1-cyclopropyl-1H-indole-4-carboxylic acid (0.376 g, 1.315 mmol, 90% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.01 (m, 2H) 1.05-1.12 (m, 2H) 3.51 (tt, J=7.07, 3.66 Hz, 1H) 6.89 (d, J=2.53 Hz, 1H) 7.52 (d, J=3.03 Hz, 1H) 7.80 (d, J=1.77 Hz, 1H) 7.99 (d, J=1.01 Hz, 1H) 13.05 (br. s., 1H). MS(ES) [M+H]+ 280.1.

Workup

  1. customwere removed in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc (2x)
  4. washThe combine organics were wash with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cba2e33165e04484942ef52fa85755ec
Source dataset
uspto-grants-2015_08
Patent number
US09114141B2

Linked notes

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