Potassium Hydroxide → tert-butyl 4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1918648Notes

Reaction equation

HRID 1918648 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.O=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 871105-ChloroindoleHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 12072032tert-butyl 4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-chloro-1H-indole (2.15 g; 13.90 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (3.08 g; 15.29 mmol) and potassium hydroxide (3.67 g; 55.6 mmol) were added in MeOH (50 mL) and heated to reflux for 24 hours. The reaction mixture was cooled to room temperature and poured into ice water (70 mL). The reaction mixture was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulphate and concentrated to give 4.52 g (98%) of tert-butyl 4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf2fdb5e285248a6aa42d9a6ebabb666
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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