Ammonium formate → HCID 10262727, compound

HRID 1683924Notes

Reaction equation

HRID 1683924 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:18]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:18]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10017985HCID 10017985, compound

Product 1

HCID 10262727HCID 10262727, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-benzylamino-3-(N-methylpyrrolidin-3-yl)-1H-indole (7.80 g, 25.5 mmol), ammonium formate (16.10 g, 255 mmol, 10 eq), and 10% Pd on carbon (0.78 g) in absolute ethanol (250 mL) was heated at reflux under nitrogen for 1 hour. The reaction was filtered, and filtrate evaporated under reduced pressure. The residual oil was column chromatographed using silica gel (approximately 200 g) and elution with 0.3% triethylamine in methanol to afford the title compound (0.90 g, 16%) as a pale yellow oil: 1H NMR (CD3OD) δ7.13 (d, J=8.5 Hz, 1H), 6.94 (br s, 2H), 6.65 (dd, J=2.0 and 8.5 Hz, 1H), 4.91 (s, 2-NH), 3.66-3.50 (m, 1H), 3.17-3.08 (br t, 1H), 2.96-2.85 (m, 1H), 2.67-2.50 (m, 2H), 2.40 (s, 3H), 2.37-2.24 (m, 1H), 2.08-1.93 (m, 1H); FAB LRMS (m/z, relative intensity) 216 (MH+, 100).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 1 hour
  3. filtrationThe reaction was filtered
  4. customfiltrate evaporated under reduced pressure
  5. customchromatographed
  6. washsilica gel (approximately 200 g) and elution with 0.3% triethylamine in methanol

Sources & evidence

ORD record
ord-69a321932dad44fd8de72018109ce9ef
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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