Ammonium formate → HCID 178488616, compound

HRID 2410726Notes

Reaction equation

HRID 2410726 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][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH:19]=[C:18]([C:30]([NH2:32])=[O:31])[C:14]=3[NH:15][C:16]=2[CH:17]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]=[C:20]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)[CH:19]=[C:18]([C:30]([NH2:32])=[O:31])[C:14]=3[NH:15][C:16]=2[CH:17]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 66604886HCID 66604886, compound

Product 1

HCID 178488616HCID 178488616, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 7-(benzyloxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (Example 206, 155 mg, 0.366 mmol), 10% palladium on activated carbon (75 mg) and ammonium formate (115 mg, 1.83 mmol) was heated at reflux for 2 hr. Filtration followed by removal of the solvent form the filtrate. The residue was suspended in methylene chloride and filtration afforded 7-hydroxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (109 mg) as a yellow solid. MS (ESI) m/z 334.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.23 (1H, br. s.), 9.75 (1H, br. s.), 8.52 (1H, br. s.), 8.17-8.26 (3H, m), 8.01 (1H, d, J=8.24 Hz), 7.79 (1H, br. s.), 7.04-7.13 (3H, m), 6.74 (1H, dd, J=8.39, 1.98 Hz), 3.85 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-5a5c0af5a7ee4b7dadac97147af2d106
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…