Hydrochloric Acid → 4-bromo-2-chloro-1H-indole

HRID 520599Notes

Reaction equation

HRID 520599 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([Cl:21])[N:6]2S(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+].Cl>CC(O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([Cl:21])[NH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682264944-Bromo-2-chloro-1-[(4-methylphenyl)sulfonyl]-1H-indole

Product 1

HCID 197003094-bromo-2-chloro-1H-indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

4-Bromo-2-chloro-1-[(4-methylphenyl)sulfonyl]-1H-indole (215 mg), IPA (2.5 ml) and 2 M NaOH (aq) (2.5 ml) were mixed in a microwave vial and heated in the microwave for 30 min at 120° C. The reaction was acidified using 2M HCl (aq) and then extracted with DCM, which was passed through a hydrophobic frit, then evaporated to dryness. The residue was triturated with methanol which was then evaporated to afford the title compound, 112 mg.

Workup

  1. extractionextracted with DCM, which
  2. customevaporated to dryness
  3. customThe residue was triturated with methanol which
  4. customwas then evaporated

Sources & evidence

ORD record
ord-d646c431cbbf481e812a3bc780829b0b
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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