HCID 22668358, compound → HCID 22668284, compound

HRID 456917Notes

Reaction equation

HRID 456917 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[N:13]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][OH: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>[Cl:1][C:2]1[C:11]([C:12]2[N:13]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH:21]=[O: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

Participants

4

Reactant 1

HCID 22668358HCID 22668358, compound

Product 1

HCID 22668284HCID 22668284, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(2-chloro-3-quinolinyl)-5-(hydroxymethyl)-1H-indole-1-carboxylate (7-2, 800 mg, 1.96 mmol, 1 equiv) and MnO2 (850 mg, 9.8 mmol, 5.00 equiv) in dichloromethane (100 mL) was heated at reflux for 1.5 hours. Additional NbO2 (700 mg, 8.05 mmol, 4.10 equiv) was added and heating was continued for 1 hour. The catalyst was filtered and washed with dichloromethane (100 mL). The combined filtrate was concentrated to give tert-butyl 2-(2-chloro-3-quinolinyl)-5-formyl-1H-indole-1-carboxylate (8-1) as a white foam. 1H NMR (500 MHz, CDCl3) δ 10.11 (s, 1H), 8.47 (d, 1H, J=8.8 Hz), 8.22 (s, 1H), 8.16 (d, 1H, J=1.0 Hz), 8.09 (d, 1H, J=8.6 Hz), 7.95 (dd, 1H, J=8.8, 1.7 Hz), 7.89 (d, 1H, J=8.1 Hz), 7.81 (br t, 1H, J=7.6 Hz), 7.64 (br t, 1H, J=7.5 Hz), 6.80 (s, 1H), 1.27 (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureheating
  4. filtrationThe catalyst was filtered
  5. washwashed with dichloromethane (100 mL)
  6. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-0284ce46333f45fdb2d9fd0bcd5e5937
Source dataset
uspto-grants-2007_03
Patent number
US07186723B2

Reaction notes

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