Stannous Chloride → methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715955Notes

Reaction equation

HRID 715955 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[N:9]3[CH2:13][CH2:14][CH2:15][C:8]3=[CH:7][C:6]=2[C:5]=1[C:16]([O:18][CH3:19])=[O:17])([O-])=O.[Sn](Cl)Cl>CO.O.C(Cl)Cl>[NH2:1][C:4]1[CH:12]=[CH:11][C:10]2[N:9]3[CH2:13][CH2:14][CH2:15][C:8]3=[CH:7][C:6]=2[C:5]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 2

HCID 24479Stannous ChlorideHCID 70984130methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2×

Product 1

HCID 86712114methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylateYield 70.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 19, 0.160 g) and tin (II) chloride (0.520 g) in methanol (6 mL) and water (0.06 mL) was heated at 60° C. for 8 hours. The resultant mixture was cooled and diluted with DCM and filtered through Celite. The filtrate was washed with 1M aqueous sodium hydroxide solution and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (0.100 g) as a brown solid.

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with 1M aqueous sodium hydroxide solution and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d7380e5f0baf49fb98ffb9f9b61fced8
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

Loading…