Ammonia → HCID 178513535, compound

HRID 2410852Notes

Reaction equation

HRID 2410852 reaction equation
[OH:1][C:2]1[C:3]2[C:4]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:12]=[C:11]([C:21]([O:23]C)=O)[C:5]=3[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1.[NH3:25]>CO>[OH:1][C:2]1[C:3]2[C:4]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:12]=[C:11]([C:21]([NH2:25])=[O:23])[C:5]=3[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178497261HCID 178497261, compound

Product 1

HCID 178513535HCID 178513535, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 9-(benzyloxy)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.28 g, 3.13 mmol), 10% Pd on carbon (0.567 g, 0.533 mmol) and ammonium formate (0.988 g, 15.7 mmol) in EtOH (8 mL) was heated at reflux for 1 hr. This was filtered and the solvent was removed from the filtrate to leave methyl 9-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.10 g) which was carried on. A suspension of methyl 9-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.1 g, 3.11 mmol) in 7 N NH3 in MeOH (40 mL) in a sealed microwave vial was heated at 80° C. for 48 h. Filtration afford 9-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide (675 mg, 1.78 mmol, 58% yield) as a solid. MS (ESI) m/z 304.12 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.36 (1H, s), 8.07-8.11 (2H, m), 7.52-7.66 (4H, m), 7.24 (1H, d, J=7.93 Hz), 6.79 (1H, d, J=7.93 Hz).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-ede2a99cd78d4b52aec6aa616406449e
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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