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

HRID 1847926Notes

Reaction equation

HRID 1847926 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 49.6%

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, 2.4 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 min. 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+1)+. Retention time 1.01 minutes.

Workup

  1. temperatureThe mixture was refluxed for 10 min
  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-a58282e9f9b54404a2de69847a687ae1
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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