Ammonium formate → HCID 59375160, compound

HRID 1811154Notes

Reaction equation

HRID 1811154 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])=[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[C:7]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[F:34])=[CH:6][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 59375144HCID 59375144, compound

Product 1

HCID 59375160HCID 59375160, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of benzyl 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-ylcarbamate (Example 50-1, 400 mg, 0.882 mmol), 10% palladium on charcoal (94 mg, 0.088 mmol) and ammonium formate (334 mg, 5.29 mmol) in methanol (20 mL) was heated at reflux for 1 h. The mixture was cooled to rt, diluted with methanol and filtered through a Celite pad. The filtrate was concentrated to give 7-amino-4-(2-fluorophenyl)-9H-carbazole-1-carboxamide in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ 11.07 (s, 1 H) 8.11 (br. s., 1 H) 7.78 (d, J=7.78 Hz, 1 H) 7.51 (d, J=2.01 Hz, 2 H) 7.35-7.47 (m, 3 H) 6.93 (d, J=7.78 Hz, 1 H) 6.79-6.84 (m, 1 H) 6.72 (d, J=8.03 Hz, 1 H) 6.24 (dd, J=8.41, 1.88 Hz, 1 H) 5.22 (s, 2 H). Mass spectrum m/z 320.1 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. filtrationfiltered through a Celite pad
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-058a12d802b54b2a973980d194c29dab
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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