Ammonium formate → HCID 178497261, compound

HRID 2410851Notes

Reaction equation

HRID 2410851 reaction equation
C([O:8][C:9]1[C:10]2[C:11]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:19]=[C:18]([C:28]([O:30][CH3:31])=[O:29])[C:12]=3[NH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[OH:8][C:9]1[C:10]2[C:11]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:19]=[C:18]([C:28]([O:30][CH3:31])=[O:29])[C:12]=3[NH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66604014HCID 66604014, compound

Product 1

HCID 178497261HCID 178497261, compoundYield 110.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 9-(benzyloxy)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.28 g, 3.13 mmol), 10% Pd on carbon (0.567 g, 0.533 mmol) and ammonium formate (0.988 g, 15.7 mmol) in EtOH (8 mL) was heated at reflux for 1 hr. This was filtered and the solvent was removed from the filtrate to leave methyl 9-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.10 g) which was carried on. A suspension of methyl 9-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.1 g, 3.11 mmol) in 7 N NH3 in MeOH (40 mL) in a sealed microwave vial was heated at 80° C. for 48 h. Filtration afford 9-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide (675 mg, 1.78 mmol, 58% yield) as a solid. MS (ESI) m/z 304.12 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.36 (1H, s), 8.07-8.11 (2H, m), 7.52-7.66 (4H, m), 7.24 (1H, d, J=7.93 Hz), 6.79 (1H, d, J=7.93 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  3. filtrationThis was filtered
  4. customthe solvent was removed from the filtrate

Sources & evidence

ORD record
ord-7be328738bce45a8a13cf9256ff6bcc4
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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