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

HRID 1014315ノート

反応式

HRID 1014315 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-edb6ae427eb840e2806aadd7942abfb5
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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