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

HRID 1014314노트

반응식

HRID 1014314 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][CH3:28].CO>ClCCl.CC(=O)OCC.[Pd].C1COCC1>[CH2:27]([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])[CH3:25])[CH3:28]

참가 물질

9

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 12219N-MethylethylamineHCID 594418341-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

생성물 1

HCID 594420161-{[ethyl(methyl)amino]acetyl}-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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-methylethanamine(1.5 g, 25.4 mmol) in 10 mL dichloromethane were added and 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 was removed under reduced pressure and the derived residue (3.4 g, 11.59 mmol) 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 H2 pressure (65 psi). The catalyst was removed via filteration, and the solvent was evaporated under reduced pressure to afford 1-{[ethyl(methyl)amino]acetyl}-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine as a yellow solid, 3.0 g (97%).1HNMR (400 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.14 Hz, 3H), 2.20 (s, 3H), 2.46(m, 2H), 2.94 (t, 2 H), 3.16(s, 2H), 3.68 (s, 3H), 4.06 (t, J=8.42 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 was removed under reduced pressure
  5. stirringthe reaction was stirred at RT overnight under H2 pressure (65 psi)
  6. customThe catalyst was removed via filteration
  7. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-3a358f2a1b3f49efad154a9ef3abcf17
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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