Sodium hydride → methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715956Notes

Reaction equation

HRID 715956 reaction equation
[H-].[Na+].CS(O[CH2:8][CH2:9][CH2:10][C:11]1[NH:12][C:13]2[CH:14]=[CH:15][C:16]([N+:24]([O-:26])=[O:25])=[C:17]([C:20]([O:22][CH3:23])=[O:21])[C:18]=2[CH:19]=1)(=O)=O>CN(C=O)C.C(OCC)(=O)C>[N+:24]([C:16]1[CH:15]=[CH:14][C:13]2[N:12]3[CH2:8][CH2:9][CH2:10][C:11]3=[CH:19][C:18]=2[C:17]=1[C:20]([O:22][CH3:23])=[O:21])([O-:26])=[O:25]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 86712115methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate2×

Product 1

HCID 70984130methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylateYield 95.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% dispersion in oil, 0.096 g) was added to a solution of methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate (Intermediate 20, 0.460 g) in DMF (12 mL) and the resultant mixture was stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and washed with water and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (0.320 g) as a brown solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0213e223de8345aea448f4bfb6dfc373
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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