1-甲基吲哚啉 → N-甲基吲哚

HRID 6704

反应方程式

HRID 6704 反应方程式
[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

参与物

4

反应物 1

HCID 558301-甲基吲哚啉

产物 1

HCID 11781N-甲基吲哚收率 57%

试剂、催化剂与溶剂 2

HCID 14801二氧化锰催化剂HCID 1140甲苯溶剂

实验过程

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 ref lux 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) δ 6.93-7.11 (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]+.

后处理

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

来源与证据

ORD记录
ord-0d4e9f47c44c454597841332d2046dc8
来源数据集
uspto-grants-2006_08
专利号
US07084152B2

关联笔记

加载中…