Ammonium formate → HCID 66605143, compound

HRID 2410821Notes

Reaction equation

HRID 2410821 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[C:18]4[N:26]=[C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=5)[CH:24]=[C:23]([C:37]([NH2:39])=[O:38])[C:19]=4[NH:20][C:21]=3[CH:22]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C(Cl)Cl.[Pd]>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]3[C:18]4[N:26]=[C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:36])[F:35])[CH:28]=5)[CH:24]=[C:23]([C:37]([NH2:39])=[O:38])[C:19]=4[NH:20][C:21]=3[CH:22]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 66605059HCID 66605059, compound

Product 1

HCID 66605143HCID 66605143, compoundYield 52.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(4-benzylpiperazin-1-yl)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (20 mg, 0.038 mmol), 10% Pd on carbon (7 mg) and ammonium formate (12 mg, 0.19 mmol) in MeOH (3 mL) was heated at reflux for 0.5 hr. The reaction was cooled to RT, diluted with DCM and filtered. The solvents were removed to leave 7-(piperazin-1-yl)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (9 mg, 0.02 mmol, 52% yield). MS (ESI) m/z 440.16 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.32 (1H, s), 8.53-8.65 (3H, m), 8.41 (1H, s), 8.07 (1H, d, J=8.85 Hz), 7.88 (1H, s), 7.69-7.83 (2H, m), 7.21 (1H, d, J=1.83 Hz), 7.00 (1H, dd, J=8.70, 1.98 Hz), 3.13-3.25 (4H, m), 2.82-3.00 (4H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 0.5 hr
  3. filtrationfiltered
  4. customThe solvents were removed

Sources & evidence

ORD record
ord-e71c26ac348e4d5981cb3623d7c2efe0
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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