Water → ethyl 1-(phenylmethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 2063281Notes

Reaction equation

HRID 2063281 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C.C(OCC)C>[CH2:17]([N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 21868741Ethyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

Product 1

HCID 44608257ethyl 1-(phenylmethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

2 g (10 mmol) of ethyl pyrrolo[2,3-b]pyridine-2-carboxylate (WO2004101563) are added, portionwise, to a suspension of 0.44 g (11 mmol) of sodium hydride in 50 ml of DMF, stirred at 20° C. After stirring at ambient temperature for 1 h, 2.1 g (12 mmol) of benzyl bromide are added, dropwise, and the reaction mixture is stirred at ambient temperature for 20 h. 150 ml of water and 150 ml of ethyl ether are subsequently added with stirring. The aqueous phase is separated and extracted twice with 50 ml of ethyl ether. The organic phases are combined, washed with 100 ml of water, dried over sodium sulphate and then concentrated under reduced pressure. The resulting product is purified by silica column chromatography, elution being carried out with a mixture of heptane and dichloromethane. 2.3 g of the expected product are thus isolated.

Workup

  1. stirringAfter stirring at ambient temperature for 1 h
  2. stirringdropwise, and the reaction mixture is stirred at ambient temperature for 20 h
  3. stirringwith stirring
  4. customThe aqueous phase is separated
  5. extractionextracted twice with 50 ml of ethyl ether
  6. washwashed with 100 ml of water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting product is purified by silica column chromatography, elution
  10. additionbeing carried out with a mixture of heptane and dichloromethane

Sources & evidence

ORD record
ord-2f75c540de484dd19b56714487b13263
Source dataset
uspto-grants-2012_10
Patent number
US08288376B2

Reaction notes

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