Ammonia → HCID 86663054, compound

HRID 2410827Notes

Reaction equation

HRID 2410827 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Br:15])[CH:12]=[C:11]([C:16]([O:18]C)=O)[C:7]=3[NH:8][C:9]=2[CH:10]=1.[NH3:20]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Br:15])[CH:12]=[C:11]([C:16]([NH2:20])=[O:18])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86663051HCID 86663051, compound

Product 1

HCID 86663054HCID 86663054, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (700 mg, 2.19 mmol) and 7 N NH3 in MeOH (5 mL) in a sealed microwave vial was heated in an oil bath at 80° C. for 16 h. After cooled to RT, the solid was collected by filtration and washed with MeOH, to afford 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxamide (500 mg, 1.15 mmol, 53% yield). MS (ESI) m/z 306.96 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.18 (1H, br. s.), 8.33 (1H, br. s.), 7.79 (1H, br. s.), 7.71-7.77 (2H, m), 6.79 (1H, s), 6.52-6.60 (1H, m), 5.70 (2H, br. s.).

Workup

  1. temperatureAfter cooled to RT
  2. filtrationthe solid was collected by filtration
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-dcb3955ace384f3296330954171afddb
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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