1-Methyl-2,3-dihydro-1H-indole → 1-Methylindole

HRID 28418

반응식

HRID 28418 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

참가 물질

4

반응물 1

HCID 558301-Methyl-2,3-dihydro-1H-indole

생성물 1

HCID 117811-Methylindole수율 57%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 1140Toluene용매

실험 절차

The N-methyl indoline product in Example 47 (70 mg, 0.22 mmol) was dissolved in toluene (9 mL) in a 50-mL flask under N2 fitted with a condenser. MnO2 (199 mg, 2.3 mmol) was added, and the mixture was heated to reflux for 1.5 h. The mixture was cooled to rt, Celite, and the pad was washed several times with liberal amounts of MeOH. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography (gradient 25-35% EtOAc/hexane) to provide the N-methyl indole product (39 mg, 57%) as an orange oil: 1H NMR (300 MHz, CDCl3) δ6.93-7.11 (m, 5H), 6.72 (d, J=8.5 Hz, 1H), 6.42 (d, J=3.1 Hz, 1H), 4.29 (t, J=5.8 Hz, 1H), 3.84-3.96 (m, 2H), 3.77 (s, 3H), 2.99 (dd, J=11.3, 5.0 Hz, 1H), 2.67 (dd, J=11.3, 6.7 Hz, 1H), 2.49 (s, 3H); ESI MS m/z=313 [C19H18F2N2+H]+.

후처리

  1. customfitted with a condenser
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1.5 h
  4. washCelite, and the pad was washed several times with liberal amounts of MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (gradient 25-35% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-f635dd3dc3a84de7a8b31f43f1b13b62
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419985B2

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