HCID 59129336, compound → 2-(1-methyl-cyclopropyl)-1H-indol-5-ylamine

HRID 468361Notes

Reaction equation

HRID 468361 reaction equation
[CH3:1][C:2]1([C:5]2[NH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][CH:8]=3)[CH2:4][CH2:3]1>CCO.[Ni]>[CH3:1][C:2]1([C:5]2[NH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([NH2:14])=[CH:9][CH:8]=3)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 59129336HCID 59129336, compound

Product 1

HCID 591295412-(1-methyl-cyclopropyl)-1H-indol-5-ylamineYield 28.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(1-methylcyclopropyl)-5-nitro-1H-indole (0.70 g, 3.2 mmol) in EtOH (20 mL) was added Raney Nickel (100 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to afford 2-(1-methyl-cyclopropyl)-1H-indol-5-ylamine (170 mg, 28%). 1H NMR (400 MHz, CDCl3) δ 7.65 (brs, 1H), 7.08 (d, J=8.4 Hz, 1H), 6.82 (s, 1H), 6.57 (d, J=8.4 Hz, 1H), 6.14 (s, 1H), 3.45 (brs, 2H), 1.47 (s, 3H), 0.82-0.78 (m, 2H), 0.68-0.63 (m, 2H).

Workup

  1. filtrationThe catalyst was filtered off through a celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-5422f4a9e75b4d6d8a7eed43dd43e7a6
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

Loading…