Ammonium formate → HCID 66604487, compound

HRID 2410691Notes

Reaction equation

HRID 2410691 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([NH:17]C(=O)OCC3C=CC=CC=3)[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].C([O-])=O.[NH4+]>[Pd].CO>[NH2:17][C:12]1[CH:13]=[C:14]2[C:9]([C:8]3[CH:7]=[C:6]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=4)[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:16]=3[NH:15]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66605755HCID 66605755, compound

Product 1

HCID 66604487HCID 66604487, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazol-2-ylcarbamate (95 mg, 0.204 mmol, Example 136), palladium on carbon (10%) (39.5 mg, 0.037 mmol) and ammonium formate (77 mg, 1.224 mmol) in MeOH (5 mL) was flushed with nitrogen and heated at reflux for 1 hr. The reaction mixture was cooled to room temperature and filtered. The solvent was removed from the filtrate to leave 7-amino-3-(3-methoxyphenyl)-9H-carbazole-1-carboxamide (68 mg, 0.189 mmol, 93% yield) as a solid. MS (ESI) m/z 332.1 (M+H). 1H NMR (MeOD) δ ppm 8.31 (1H, d, J=1.53 Hz), 8.02 (1H, d, J=1.53 Hz), 7.89 (1H, d, J=8.24 Hz), 7.26 -7.47 (3H, m), 6.83-7.01 (2H, m), 6.71 (1H, dd, J=8.24, 1.83 Hz), 3.91 (3H, s).

Workup

  1. customwas flushed with nitrogen
  2. temperatureheated
  3. temperatureat reflux for 1 hr
  4. filtrationfiltered
  5. customThe solvent was removed from the filtrate

Sources & evidence

ORD record
ord-36bbc61cf7334334a312f8e47357160b
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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