HCID 22583463, compound → HCID 58787186, compound

HRID 1375430Notes

Reaction equation

HRID 1375430 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH2:15][CH2:14]3)(=[O:10])=[O:9])[CH2:4][CH2:3]1>ClCCl.O=[Mn]=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)(=[O:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 22583463HCID 22583463, compound

Product 1

HCID 58787186HCID 58787186, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-[(4-methylpiperazin-1-yl)sulfonyl]indoline (1-7, 8.00 g, 28.4 mmol, 1 equiv) and MnO2 (8.00 g, 92.0 mmol, 3.24 equiv) in dichloromethane (300 mL) was heated at reflux for 1 hour. More MnO2 (8.00 g, 92.0 mmol, 3:24 equiv) was added, and the resulting suspension was heated for 2 hours. The manganese oxides were filtered off onto a pad of celite and washed with dichloromethane (500 mL). The filtrate was concentrated to give 5-[(4-methylpiperazin-1-yl) sulfonyl]-1H-indole (1-8) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.59 (br s, 1H), 8.10 (d, 1H, J=1.8 Hz), 7.55 (dd, 1H, J=8.5, 1.8 Hz), 7.46 (d, 1H, J=8.5 Hz), 7.34 (m, 1H), 6.67 (m, 1H), 3.04 (br m, 4H), 2.48 (br t, 4H, J=4.9 Hz), 2.25 (s, 3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe resulting suspension was heated for 2 hours
  4. filtrationThe manganese oxides were filtered off onto a pad of celite
  5. washwashed with dichloromethane (500 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3d536e909ccf4559bb27f1367650d810
Source dataset
uspto-grants-2007_01
Patent number
US07169788B2

Reaction notes

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