Sodium hydride → 3-(5,6-dimethyl-pyridine-3-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 226930Notes

Reaction equation

HRID 226930 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])[CH:5]=[N:6][C:7]=1[CH3:8].[H-].[Na+].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)[CH:12]=2)=[O:10])[CH:5]=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 125437332-(Bromomethyl)-6-methylpyridineHCID 577545393-(5,6-Dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

Product 1

HCID 167311733-(5,6-dimethyl-pyridine-3-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4h was prepared following the procedure described in Step 3 of Example 1. Briefly described here, 65 mg (0.23 mmol) of 3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one 3c, 11 mg (0.28 mmol) of 60% sodium hydride and 52 mg (0.28 mmol) of 2-bromomethyl-6-methyl-pyridine (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351) in 0.7 mL N,N-dimethylformamide were stirred at rt for 2 h. The product was purified using reverse phase HPLC, mobile phase with a gradient 10-70% acetonitrile in 50 min. HPLC fractions containing pure product 4h were lyophilized to give 41 mg of a white solid as trifluoroacetate salt: LC-MSD, m/z for C24H21N3O2 [M+H]+=384.5, HPLC retention time: 0.4 min; 1H NMR (400 MHz, CDCl3): δ 2.5 (s, 3H), 2.8 (s, 3H), 2.85 (s, 3H), 6.05 (s, 2H), 7.2-7.3 (m, 1H), 7.4-7.5 (m, 2H), 7.5-7.6 (m, 1H), 7.6-7.7 (m, 1H), 8.0-8.1 (m, 1H), 8.3-8.4 (m, 1H), 8.4 (s, 1H), 8.7 (s, 1H), 8.9 (s, 1H).

Workup

  1. customThe product was purified
  2. customin 50 min
  3. additionHPLC fractions containing pure product 4h

Sources & evidence

ORD record
ord-73ed51ce0d61494794c6b6672cb92f81
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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