Sodium hydride → HCID 57754594, compound

HRID 227131Notes

Reaction equation

HRID 227131 reaction equation
[I:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=1>CN(C=O)C>[I:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123768444-Quinolinol, 3-iodo-HCID 125437332-(Bromomethyl)-6-methylpyridine

Product 1

HCID 57754594HCID 57754594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-iodo-1H-quinolin-4-one (1.36 g, 5 mmol, 1 equiv) in 5 mL of DMF was treated with 0.22 g of NaH (1.1 equiv) for 10 min. 2-Bromomethyl-6-methyl-pyridine (1.11 g, 1.2 equiv) was then added and stirring continued for 3 h. The reaction was quenched by slow addition of saturated aqueous solution of NH4Cl. Standard workup followed by flash chromatography gave 3-iodo-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one as a white solid.

Workup

  1. customThe reaction was quenched by slow addition of saturated aqueous solution of NH4Cl

Sources & evidence

ORD record
ord-e1c0e13858044adc80ba0bd2b5d2f4a6
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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