Ammonium formate → HCID 178513536, compound

HRID 2410772Notes

Reaction equation

HRID 2410772 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]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]([NH2:30])=[O:29])[C:14]=3[NH:15][C:16]=2[CH:17]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]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]([NH2:30])=[O:29])[C:14]=3[NH:15][C:16]=2[CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66605317HCID 66605317, compound

Product 1

HCID 178513536HCID 178513536, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-(benzyloxy)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide (880 mg, 2.237 mmol), 10% Pd on carbon (400 mg) and ammonium formate (705 mg, 11.2 mmol) in ethanol (50 mL) was heated at reflux for 1 hr. Filtration followed by removal of the solvent from the filtrate left 7-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide (658 mg, 2.17 mmol, 97% yield) as a yellow solid. MS (ESI) m/z 304.0 (M+H). 1H NMR (500 MHz, DMSO-d6) d ppm 11.30 (1H, br. s.), 9.77 (1H, br. s.), 8.54 (1H, br. s.), 8.30 (1H, s), 8.27 (2H, d, J=7.32 Hz), 8.03 (1H, d, J=8.24 Hz), 7.80 (1H, br. s.), 7.53 (2H, t, J=7.63 Hz), 7.41 (1H, s), 7.36-7.46 (1H, m), 7.14-7.15 (1H, m), 7.14-7.14 (1H, m), 7.12 (1H, d, J=1.83 Hz), 6.75 (1H, dd, J=8.55, 2.14 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  3. filtrationFiltration
  4. customfollowed by removal of the solvent from the filtrate

Sources & evidence

ORD record
ord-908ed8cab0084a0cafd3e2f26da8e2f6
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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