Acetic Acid → 3-(Pyridin-2-yl)-1H-indole

HRID 66565Notes

Reaction equation

HRID 66565 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[C:7](C(=O)CS(C)(=O)=O)[NH:8]2)=[CH:4][C:3]=1Cl.[BH4-].[Na+].C(O)(=O)C.C>C(O)C>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:6]1[C:5]2[C:9](=[CH:10][CH:2]=[CH:3][CH:4]=2)[NH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 4311764Sodium borohydrideHCID 130345866-Bromo-5-chloro-2[(methylsulfonyl)acetyl]-3-(2-pyridyl)indole

Product 1

HCID 143380963-(Pyridin-2-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6-bromo-5-chloro-2[(methylsulfonyl)acetyl]-3-(2-pyridyl)indole (2.2 g) in 75 ml of ethanol add 0.175 g of sodium borohydride. After a solution is obtained (about 10 minutes) stir the mixture of another 30 minutes, then slowly add 2 ml of acetic acid. Treat with charcoal, filter and add 100 ml of water to the filtrate to obtain 6-bromo-5-chloro-2[1-hydroxy-2-methylsulfonyl)ethyl]-3-(2-pyridyl)indole.

Workup

  1. customAfter a solution is obtained (about 10 minutes)
  2. additionthe mixture of another 30 minutes
  3. filtrationfilter
  4. additionadd 100 ml of water to the filtrate

Sources & evidence

ORD record
ord-1deef84b26d6447797ae878fcc23f1b5
Source dataset
uspto-grants-1982_08
Patent number
US04342769

Reaction notes

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