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

HRID 28418

反応式

HRID 28418 の反応式
[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

参加物

4

反応物 1

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

生成物 1

HCID 117811-Methylindole収率 57%

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 1140Toluene溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-f635dd3dc3a84de7a8b31f43f1b13b62
出典データセット
uspto-grants-2008_09
特許番号
US07419985B2

関連ノート

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