Ammonia → HCID 66606459, compound

HRID 2410817Notes

Reaction equation

HRID 2410817 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:16]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:14]=[C:13]([C:27]([O:29]C)=O)[C:9]=3[NH:10][C:11]=2[CH:12]=1)([O-:3])=[O:2].[NH3:31]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:16]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[CH:18]=4)[CH:14]=[C:13]([C:27]([NH2:31])=[O:29])[C:9]=3[NH:10][C:11]=2[CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66605774HCID 66605774, compound

Product 1

HCID 66606459HCID 66606459, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of methyl 7-nitro-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (250 mg, 0.602 mmol) in 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 cooling to RT, the solid was collected by filtration and washed with MeOH to afford 7-nitro-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (200 mg, 0.475 mmol, 79% yield). MS (ESI) m/z 401.1 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.26 (1H, br. s.), 8.62-8.81 (5H, m), 8.54 (1H, d, J=8.85 Hz), 8.03-8.19 (2H, m), 7.75-7.88 (2H, m).

Workup

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

Sources & evidence

ORD record
ord-3962071462f94d64a936898b593d440e
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…