Ammonia → HCID 86663061, compound

HRID 2410838Notes

Reaction equation

HRID 2410838 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:21]([O:23]C)=O)[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.[NH3:25]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:21]([NH2:25])=[O:23])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86663060HCID 86663060, compound

Product 1

HCID 86663061HCID 86663061, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Methyl 2-bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxylate (3.0 g, 7.69 mmol) was mixed with 7 N NH3 in MeOH (80 mL) in a pressure bottle. This was sealed and heated at 75° C. for 47 hrs. It was cooled to RT and the solid was collected by filtration, washed with MeOH, and air dried to afford 2-bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (2.64 g, 6.33 mmol, 82% yield) as a yellow solid. MS (ESI) m/z 375.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δppm 11.41 (1H, s), 8.42 (1H, br. s.), 7.96 (1H, d, J=8.85 Hz), 7.85-7.91 (2H, m), 7.19 (1H, d, J=1.83 Hz), 7.03 (1H, dd, J=8.70, 1.98 Hz), 3.72-3.85 (4H, m), 3.16-3.25 (4H, m).

Workup

  1. customThis was sealed
  2. temperatureIt was cooled to RT
  3. filtrationthe solid was collected by filtration
  4. washwashed with MeOH, and air
  5. customdried

Sources & evidence

ORD record
ord-a4d4bbbe284f4fe3a807bf8cc187b602
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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