Ammonium formate → 6-fluoro-1,1-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-amine

HRID 468524Notes

Reaction equation

HRID 468524 reaction equation
[F:1][C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]2[CH:6]=[C:7]3[C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:1][C:2]1[C:3]([NH2:16])=[CH:4][C:5]2[CH:6]=[C:7]3[C:13]([CH3:14])([CH3:15])[CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59129578HCID 59129578, compound

Product 1

HCID 581832876-fluoro-1,1-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-amineYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-fluoro-1,1-dimethyl-7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole (600 mg, 24 mmol) in ethanol (15 mL) was added ammonium formate (600 mg, 9.5 mmol) and Pd/C (10%, 129 mg, 0.12 mmol). The mixture was refluxed for 10 mm, The Pd catalyst was removed via filtration through Celite and washed with ethanol. The filtrate was concentrated and purified by column chromatography (20-40% ethyl acetate-hexanes) to provide 6-fluoro-1,1-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-amine (260 mg, 49%). ESI-MS m/z calc. 218.1, found 219.2 (M+W. Retention time 1.01 minutes.

Workup

  1. temperatureThe mixture was refluxed for 10 mm
  2. customThe Pd catalyst was removed via filtration through Celite
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography (20-40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-9159f5c937214e9b80c368b90b25e6ea
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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