Potassium Carbonate → 5-(methyloxy)-1-{[methyl(propyl)amino]acetyl}-2,3-dihydro-1H-indol-6-amine

HRID 1014315Notes

Reaction equation

HRID 1014315 reaction equation
Br[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH3:25][NH:26][CH2:27][CH2:28][CH3:29]>ClCCl>[CH3:18][O:17][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][C:11]=1[NH2:14])[N:5]([C:3](=[O:4])[CH2:2][N:26]([CH3:25])[CH2:27][CH2:28][CH3:29])[CH2:6][CH2:7]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12315N-MethylpropylamineHCID 594418341-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 594419915-(methyloxy)-1-{[methyl(propyl)amino]acetyl}-2,3-dihydro-1H-indol-6-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 1-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (4.0 g, 12.7 mmol) was dissolved in 50 mL of dichloromethane, then K2CO3 (4.4 g, 31.7 mmol) and N-methyl-1-propanamine (1.9 g, 25.4 mmol) in 10 mL dichloromethane were added, the reaction was stirred at RT for 3 hours. After filtration, the organic layers were washed with water (2×100 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting residue was dissolved in 10 mL of EA , 25 mL of MeOH and 15 mL of THF, then 0.8 g 10% Pd/C was added and the reaction was stirred at RT overnight under H2 pressure (65 psi). The catalyst was removed via filtration and the solvent was removed under reduced pressure to afford 5-(methyloxy)-1-{[methyl(propyl)amino]acetyl}-2,3-dihydro-1H-indol-6-amine as a yellow solid, 3.0 g (96%). 1HNMR (400 MHz, DMSO-d6) δ ppm: 0.81 (t, J=7.14 Hz, 3H), 1.40 (m, 2H), 2.21 (s, 3H), 2.35(m, 2H), 2.94 (t, J=8.24 Hz, 2 H), 3.17(s, 2H), 3.70 (s, 3H), 4.07 (t, J=8.33 Hz, 2 H), 4.60 (s, 2H), 6.67 (s, 1 H), 7.52 (s, 1 H).

Workup

  1. filtrationAfter filtration
  2. washthe organic layers were washed with water (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe resulting residue was dissolved in 10 mL of EA
  6. addition25 mL of MeOH and 15 mL of THF, then 0.8 g 10% Pd/C was added
  7. stirringthe reaction was stirred at RT overnight under H2 pressure (65 psi)
  8. customThe catalyst was removed via filtration
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-edb6ae427eb840e2806aadd7942abfb5
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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