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

HRID 1014317노트

반응식

HRID 1014317 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[CH2:29][CH2:28][CH:27]([OH:30])[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[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26]2)=[CH:9][C:10]=1[O:17][CH3:18]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 594418341-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

생성물 1

HCID 594420191-{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-3-pyrrolidinol수율 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-pyrrolidinol (1.33 g, 15.2 mmol) in 10 mL dichloromethane were added, and 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, 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-{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-3-pyrrolidinol as a white solid (3.0 g, 92%).1H NMR (400 MHz, DMSO-d6) δ ppm: 1.60 (m, 1 H), 1.97 (m, 1 H), 2.47(s, 1H), 2.59 (m, 1 H), 2.72 (m, 1 H), 2.85 (m, 1 H), 2.96 (m, 4 H), 3.50(s, 2H), 3.68(s, 3H), 4.00 (t, J=8.33 Hz, 2 H), 4.86 (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 a balloon of H2 pressure
  7. customThe catalyst was removed via filtration
  8. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-bb6508a9c146461589866c245d60c50d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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