Ethanol → 5-Bromo-3-isopropyl-1H-indole-7-carboxylic acid

HRID 1616799Notes

Reaction equation

HRID 1616799 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=C(C#N)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:13]([CH3:15])[CH3:14].[OH-:16].[Na+].[CH3:18][CH2:19][OH:20]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:18]([C:19]([OH:16])=[O:20])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 678165455-Bromo-3-isopropyl-1H-indole-7-carbonitrile

Product 1

HCID 678183425-Bromo-3-isopropyl-1H-indole-7-carboxylic acidYield 129%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 5-bromo-3-(1-methylethyl)-1H-indole-7-carbonitrile (1.66 g, 6.31 mmol) in EtOH (45 mL) and water (15 mL) was added 6 N NaOH (10 mL, 60.0 mmol). The reaction was heated at reflux (100° C. oil bath) under N2 for 72 h. LCMS showed that the reaction was complete after 24 h. The reaction was cooled to RT, evaporated to near dryness, diluted with water (˜100 mL), and acidified with 6 N HCl (10 mL). The suspension was triturated, filtered, washed with water and dried under vacuum to give the product 5-bromo-3-(1-methylethyl)-1H-indole-7-carboxylic acid (2.29 g, 8.12 mmol, 129% yield) as an off-white solid. MS (ES)+ m/e 282.4 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureThe reaction was cooled to RT
  3. customevaporated
  4. additiondiluted with water (˜100 mL)
  5. customThe suspension was triturated
  6. filtrationfiltered
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-c9e1e6a5875d4b8e87818c76b55d20ef
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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