HCID 86663049, compound → HCID 86663051, compound

HRID 2410826Notes

Reaction equation

HRID 2410826 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N+:15]([O-])=O)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1>[Ni].C1COCC1>[NH2:15][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]=[C:2]([Br:1])[CH:3]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:5]=3[NH:6][C:7]=2[CH:8]=1

Participants

4

Reactant 1

HCID 86663049HCID 86663049, compound

Product 1

HCID 86663051HCID 86663051, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl 2-bromo-7-nitro-5H-pyrido[3,2-b]indole-4-carboxylate (1.00 g, 2.86 mmol) and Raney nickel (1.0 g, 17 mmol, 2800 nickel slurry in water) was stirred in THF (50 mL) under H2 (balloon) for 1.5 hr. This was filtered and the filter cake was washed with warn THF (100 mL). Removal of the solvent left methyl 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (700 mg, 2.08 mmol, 73% yield) as a solid. MS (ESI) m/z 321.94 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.27 (1H, br. s.), 7.78 (1H, d), 7.62 (1H, s), 6.79 (1H, br. s.), 6.60 (1H, d, J=8.5), 5 84 (2H, br. s.), 4.00 (3H, s).

Workup

  1. filtrationThis was filtered
  2. washthe filter cake was washed
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-67e158cbeace4ce1b23c7de5e6db10ae
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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