Ethanol → HCID 11395048, compound

HRID 1602375Notes

Reaction equation

HRID 1602375 reaction equation
[C:1]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([Cl:15])[CH:11]=[C:10]([Cl:16])[CH:9]=2)([O:3][CH2:4][CH3:5])=[O:2].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]#[N:25])[CH:18]=1.N1CCCC[CH2:27]1.C(O)C>C(OCC)C>[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](/[C:23](=[CH:27]/[C:14]2[C:13]3[C:8](=[CH:9][C:10]([Cl:16])=[CH:11][C:12]=3[Cl:15])[NH:7][C:6]=2[C:1]([O:3][CH2:4][CH3:5])=[O:2])/[C:24]#[N:25])[CH:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 809233-PyridineacetonitrileHCID 2736407ethyl 4,6-dichloro-1H-indole-2-carboxylate

Product 1

HCID 11395048HCID 11395048, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 2-carboethoxy-4,6-dichloroindole (1.43 g, 5.0 mmol), pyrid-3-ylacetonitrile (0.59 g, 5.0 mmol), piperidine (0.2 mL), and ethanol (30 mL). Heat to reflux. After 16 hours, cool to ambient temperature. Add diethyl ether to give a solid. Filter, rinse with diethyl ether, dry, recrystallize from acetone/water, filter, and dry to give the title compound: mp; 233-234° C. (dec). 1H NMR (DMSO-d6) δ 12.41 (br s, 1H), 8.86 (s, 1H), 8.57 (d, 1H, J=1 Hz), 8.16 (s, 1H), 7.94 (d, 1H, J=6.1 Hz), 7.41-7.36 (m, 1H), 7.41 (s, 1H), 7.06 (m, 1H), 4.30 (q, 2H, J=7.05 Hz), 1.23 (t, 3H, J=7.05 Hz).

Workup

  1. temperatureHeat to reflux
  2. filtrationFilter
  3. washrinse with diethyl ether
  4. customdry
  5. customrecrystallize from acetone/water
  6. filtrationfilter
  7. customdry

Sources & evidence

ORD record
ord-229bea2370be4ea197f9027feef8e94f
Source dataset
uspto-grants-1999_11
Patent number
US05981553

Reaction notes

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