Ammonium formate → HCID 10988959, compound

HRID 392764Notes

Reaction equation

HRID 392764 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([N+:19]([O-])=O)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:8]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:9])=[CH:18]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11087453HCID 11087453, compound2×

Product 1

HCID 10988959HCID 10988959, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 59, (4-Methyl-piperazin-1-yl)-(5-nitro-1H-indol-2-yl)-methanone (1.8 g) was dissolved in CH3OH (50 mL). At room temperature, ammonium formate (3.94 g) was added, followed by 10% palladium on carbon (0.66 g). The reaction mixture was heated to reflux for forty min, cooled and filtered through celite pad. The filtrate was concentrated and the residue was purified via silica gel chromatography (3-10% 2 M ammonia in methanol/dichloromethane) to give the title compound (1.60 g). 1H NMR (400 MHz, CDCl3): δ 10.46 (br s, 1H), 7.12 (d, J=8.80 Hz, 1H), 6.81 (d, J=2.15 Hz, 1H), 6.64 (dd, J=2.15, 6.46 Hz, 1H), 6.54 (d, J=1.37 Hz, 1H), 3.88 (br m, 4H), 3.70 (br s, 2H), 2.40 (t, J=4.70 Hz, 4H), 2.25 (s, 3H). MS (electrospray): exact mass calculated for C14H18N4O, 258.15; m/z found, 259.1 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for forty min
  3. temperaturecooled
  4. filtrationfiltered through celite pad
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified via silica gel chromatography (3-10% 2 M ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-e769e2a549a84c049e702ff16f79a9d6
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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