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

HRID 1014315노트

반응식

HRID 1014315 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-edb6ae427eb840e2806aadd7942abfb5
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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