Ammonium formate → HCID 10967174, compound

HRID 392765Notes

Reaction equation

HRID 392765 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][CH:15]=[CH:14][C:13]=3[N+:19]([O-])=O)=[O:9])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[NH:11][C:10]([C:8]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)=[O:9])=[CH:18]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10957150HCID 10957150, compound

Product 1

HCID 10967174HCID 10967174, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 8, (4-Methyl-piperazin-1-yl)-(7-nitro-1H-indol-2-yl)-methanone (6.4 g, 22.2 mmol), was dissolved in CH3OH (110 mL). At room temperature, ammonium formate (14.0 g, 222 mmol) was added, followed by 10% palladium on carbon (2.4 g, 2.22 mmol). The reaction mixture was heated to reflux for forty min, cooled, and then filtered through a 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 (4.4 g, 76.7%) as an off-white solid. 1H NMR (400 MHz, CDCl3/CD3OD): δ 7.08 (d, J=7.83 Hz, 1H), 6.94 (t, J=7.83 Hz, 1H), 6.73 (s, 1H), 6.58 (d, J=7.63 Hz, 1H), 4.12 (s, 2H), 3.92 (br s, 4H), 2.51 (br s, 4H), 2.34 (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 a 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-5b113689a7a14a0388d8e56c457ad25b
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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