HCID 59129495, compound → HCID 59129419, compound

HRID 1908453Notes

Reaction equation

HRID 1908453 reaction equation
[CH3:1][C:2]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-])=O)=[CH:12][CH:11]=2)([CH3:7])[C:3]([O:5][CH3:6])=[O:4]>[Ni].CO>[NH2:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:2]([CH3:7])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[CH:16]2

Participants

4

Reactant 1

HCID 59129495HCID 59129495, compound

Product 1

HCID 59129419HCID 59129419, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 2-methyl-2-(5-nitro-1H-indol-2-yl)propanoate (60 mg, 0.23 mmol) and Raney Nickel (10 mg) in MeOH (5 mL) was hydrogenated under hydrogen (1 atm) at room temperature overnight. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give methyl 2-(5-amino-1H-indol-2-yl)-2-methylpropanoate (20 mg, 38%). 1H NMR (400 MHz, CDCl3) δ 8.37 (br s, 1H), 7.13 (d, J=8.4 Hz, 1H), 6.87 (d, J=2.0 Hz, 1H), 6.63 (dd, J=2.0, 8.4 Hz, 1H), 6.20 (d, J=1.2 Hz, 1H), 3.72 (d, J=7.6 Hz, 3H), 3.43 (br s, 1H), 1.65 (s, 6H); MS (ESI) m/e (M+H+) 233.2.

Workup

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

Sources & evidence

ORD record
ord-d43fb416653b45919f47be0afa4f81e0
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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