Potassium Carbonate → 1-{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-3-piperidinol

HRID 1014318노트

반응식

HRID 1014318 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+].[NH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([OH:31])[CH2:26]1>ClCCl.O>[NH2:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][N:5]2[C:3](=[O:4])[CH2:2][N:25]2[CH2:30][CH2:29][CH2:28][CH:27]([OH:31])[CH2:26]2)=[CH:9][C:10]=1[O:17][CH3:18]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 232933-HydroxypiperidineHCID 594418341-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

생성물 1

HCID 594416491-{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-3-piperidinol수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 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 3-piperidinol (1.54 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), dried over Na2SO4 and the solvent was removed under reduced pressure. 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, the reaction was stirred at RT overnight under balloon H2 pressure. The catalyst was removed via filtration and the solvent was removed under reduced pressure to yield 1-{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-3-piperidinol as a white solid (3.0 g, 92%). 1HNMR (400 MHz, DMSO-d6) δ ppm: 1.09 (m, 1 H), 1.44 (m, 1 H), 1.62 (m, 1 H), 1.74 (m, 1H), 2.14(br, 1H), 2.47(s, 1H), 2.74(br, 2H), 2.95 (m, 4H), 3.50(s, 2H), 3.68(s, 3H), 4.04 (t, J=6.13 Hz,2 H), 4.71 (s, 2H), 6.68 (s, 1 H), 7.51 (s, 1 H).

후처리

  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 balloon H2 pressure
  7. customThe catalyst was removed via filtration
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-6d3651031a4445b79ba3df341e00ae04
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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