HCID 22668336, compound → HCID 22668263, compound

HRID 1007657Notes

Reaction equation

HRID 1007657 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[N:13]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH:21]([OH:23])[CH3:22])=[CH:16][CH:15]=3)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>ClCCl.O=[Mn]=O>[C:21]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:12]([C:11]1[C:2]([Cl:1])=[N:3][C:4]3[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:20]2)(=[O:23])[CH3:22]

Participants

4

Reactant 1

HCID 22668336HCID 22668336, compound

Product 1

HCID 22668263HCID 22668263, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2-chloro-3-quinolinyl)-5-(1-hydroxyethyl)-1H-indole-1-carboxylate (8-2, 840 mg, 1.99 mmol, 1 equiv) and MnO2 (863 mg, 9.93 mmol, 5.00 equiv) in dichloromethane (30 mL) was heated at reflux for 1 h. Additional MnO2 (500 mg, 5.75 mmol, 2.89 equiv) was added and heating was continued for 1 h. The catalyst was filtered and washed with dichloromethane (100 mL). The combined filtrate was concentrated to give tert-butyl 5-acetyl-2-(2-chloro-3 quinolinyl)-1H-indole-1-carboxylate (8-3) as a white foam. 1H NMR (500 MHz, CDCl3) δ 8.38 (d, 1H, J=8.8 Hz), 8.27 (d, 1H, J=0.7 Hz), 8.21 (s, 1H), 8.09 (d, 1H, J=8.3 Hz), 8.04 (dd, 1H, J=8.8, 1.2 Hz), 7.89 (d, 1H, J=8.1 Hz), 7.80 (br t, 1H, J=7.6 Hz), 7.63 (br t, 1H, J=7.5 Hz), 6.76 (s, 1H), 2.70 (s, 3H), 1.27 (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperatureheating
  4. filtrationThe catalyst was filtered
  5. washwashed with dichloromethane (100 mL)
  6. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-dd87863bb9274d71adf5e100b340bf84
Source dataset
uspto-grants-2004_09
Patent number
US06794393B1

Reaction notes

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