3-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-7-nitro-1H-indole → 3-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-1H-indol-7-ylamine

HRID 13702Notes

Reaction equation

HRID 13702 reaction equation
[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([N+:22]([O-])=O)[CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:25])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]>[Pd].C(O)C>[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([NH2:22])[CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:25])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 115736303-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-7-nitro-1H-indole

Product 1

HCID 115513163-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-1H-indol-7-ylamineYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenate a mixture of 3-(1-ethyl-5-fluoro-indan-1-yl)-1-methyl-7-nitro-1H-indole (0.26 g, 0.77 mmol) and 5% palladium on carbon (26 mg) in ethanol (50 ml) at 60 psi at room temperature overnight. Filter catalyst and concentrate under high vacuum to obtain the title compound as oil (0.17 g, 71%). NMR (400 MHz, CDCl3): δ 0.83 (t, 3H), 2.05 (m, 1H), 2.25 (m, 2H), 2.60 (m, 1H), 2.96 (m, 2H), 3.72 (broad s, 2H, NH2), 4.02 (s, 3H), 6.43 (m, 2H), 6.76 (d, 2H), 6.83 (t, 1H), 6.97 (d, 1H), 7.02 (m, 1H).

Workup

  1. concentrationFilter catalyst and concentrate under high vacuum

Sources & evidence

ORD record
ord-77169ae3cd4349f7918a786c2cfb0925
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Reaction notes

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