Hydrochloric Acid → Ethyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate
Reaction equation
C([Li])CCC.[C:6]([NH:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)(OC(C)(C)C)=O.[C:21]([O:26][CH2:27][CH3:28])(=[O:25])C([O-])=O.Cl.[OH-].[Na+]>C1COCC1>[NH:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[CH:20]=[C:6]1[C:21]([O:26][CH2:27][CH3:28])=[O:25]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
30 ml of n-butyllithium are added, under nitrogen, at a temperature of less than 5° C., to 5 g of 2-(N-Boc)amino-3-methylpyridine in 100 ml of THF. After stirring for 1 hour at 0° C., the lithiated derivative thus formed is added to a solution of 7 g of ethyl oxalate in 50 ml of THF at −3° C. The reaction medium is allowed to return to RT and is then poured slowly into 25 ml of 6N HCl at 0° C., while maintaining the temperature below 100° C. This mixture is heated at 50° C. for 2 hours and the pH is then brought to 3 by addition of 1N NaOH. This mixture is extracted with Et2O and the organic phase is taken up in K2CO3 solution and then dried and evaporated to give 1.8 g of the expected compound in the form of white crystals: m.p.=162° C.
Workup
- customthe lithiated derivative thus formed
- customto return to RT
- temperaturewhile maintaining the temperature below 100° C
- temperatureThis mixture is heated at 50° C. for 2 hours
- extractionThis mixture is extracted with Et2O
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-5eacf8abe47249b2bf675e8b2c180ddb
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380230B1
Reaction notes
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