Sodium hydride → 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 227024

Reaction equation

HRID 227024 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].[Br:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]Br)[N:21]=1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([Br:19])[N:21]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 220876Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 577546321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl esterYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.75 g (40.3 mmol) of 4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester was dissolved/suspended in 100 mL DMF followed by the addition of 1.93 g (48.3 mmol) of 60% sodium hydride. After the bubbling has ceased 12.1 g (48.3 mmol) of 2-bromo-6-bromomethyl-pyridine was added and the solution was stirred at r.t. overnight. The reaction was quenched using 900 mL of water, filtered and washed with 200 mL of water. The solid was further washed with 100 mL DCM. The DCM washes were evaporated and chromatographed on silica using 0-30% methanol in DCM. The purified compound was combined with the washed solid to give 14.9 g of the product as an off-white solid.

Workup

  1. additionwas added
  2. customThe reaction was quenched
  3. filtrationfiltered
  4. washwashed with 200 mL of water
  5. washThe solid was further washed with 100 mL DCM
  6. customThe DCM washes were evaporated
  7. customchromatographed on silica using 0-30% methanol in DCM

Sources & evidence

ORD record
ord-6139dc9232574fd0abfb59b5f47335a6
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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