Hydrochloric Acid → 6-Bromo-5-chloro-2[(methylthio) (methoxy)acetyl]-3-(2-pyridyl)indole

HRID 28231Notes

Reaction equation

HRID 28231 reaction equation
Cl.[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[C:8]([C:12](=[O:17])[CH2:13][S:14]([CH3:16])=O)[NH:9]2)=[CH:5][C:4]=1[Cl:24].[OH2:25].[CH3:26]O>O1CCCC1>[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[C:8]([C:12](=[O:17])[CH:13]([S:14][CH3:16])[O:25][CH3:26])[NH:9]2)=[CH:5][C:4]=1[Cl:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 173465Sch 24937

Product 1

HCID 205304266-Bromo-5-chloro-2[(methylthio) (methoxy)acetyl]-3-(2-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2 ml of concentrated hydrochloric acid to 6-bromo-5-chloro-2[(methylsulfinyl)acetyl]-3-(2-pyridyl)indole (5.0 g) in 50 ml of methanol and 50 ml of tetrahydrofuran, warm the mixture to 60° for 2 hours. Cool, add water and the resulting solid is collected and dried to obtain 6-bromo-5-chloro-2[(methylthio)(methoxy)acetyl]-3-(2-pyridyl)indole.

Workup

  1. temperaturewarm the mixture to 60° for 2 hours
  2. temperatureCool
  3. customthe resulting solid is collected
  4. customdried

Sources & evidence

ORD record
ord-87e8159487e44a049aa2a518fdc3d931
Source dataset
uspto-grants-1980_09
Patent number
US04225711

Reaction notes

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