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

HRID 1014316ノート

反応式

HRID 1014316 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][O:29][CH3:30]>ClCCl.O>[CH3:25][N:26]([CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([NH2:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4])[CH2:27][CH2:28][O:29][CH3:30]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 300977(2-Methoxyethyl)(methyl)amineHCID 594418341-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

生成物 1

HCID 594420431-({methyl[2-(methyloxy)ethyl]amino}acetyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine収率 89%

試薬・触媒・溶媒 2

HCID 962Water溶媒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-2-(methyloxy)ethanamine (1.4 g, 15.2 mmol) in 10 mL dichloromethane were added, the reaction was stirred at RT overnight. The reaction mixture was diluted with 100 mL of water, the organic solvents 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 a balloon of H2 pressure. The catalyst was removed via filtration and the solvent was evaporated under reduced pressure to yield the 1-({methyl[2-(methyloxy)ethyl]amino}acetyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine as a white solid (3.1 g, 89%). 1HNMR (400 MHz, DMSO-d6) δ ppm: 2.28(s, 3H), 2.62 (t, J=5.77 Hz, 2H), 2.94 (t, J=8.24 Hz 2 H), 3.19 (s, 3H), 3.25(s, 2H), 3.41 (t, J=5.77 Hz, 2 H), 3.68(s, 3H), 4.04 (t, J=8.33 Hz,2H), 4.61 (s, 2H), 6.67 (s, 1 H), 7.52 (s, 1 H).

後処理

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

出典と根拠

ORDレコード
ord-03afc13d513e4eec95955f5248a6f95e
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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