Chloroform → 7-Methyl-5-nitro-1H-indole

HRID 1637332Notes

Reaction equation

HRID 1637332 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.[CH3:14][Sn](C)(C)C.C(Cl)(Cl)Cl>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:14][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 6212ChloroformHCID 11661TetramethyltinHCID 3234907-Bromo-5-nitroindoline

Product 1

HCID 154534667-Methyl-5-nitro-1H-indoleYield 74.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 7-bromo-5-nitroindoline (0.65 g, 2.7 mmol) in 10 mL of DMF were added tetramethyltin (1.0 mL, 7.3 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.10 g) in a portion and resulting mixture was stirred in sealed tube for 12 h at 140° C. The reaction mixture was concentrated in vacuo, providing a dark oily residue which was subjected to column chromatography (CHCl3, neat) to yield 0.35 g (2.0 mmol, 74%) of the desired product.

Workup

  1. customresulting mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customproviding a dark oily residue which

Sources & evidence

ORD record
ord-dd7dfc58890a4692ba9cddb24bf1c608
Source dataset
uspto-grants-2000_03
Patent number
US06040451

Reaction notes

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