Sodium hydride → 3-(3,4-Dimethyl-benzoyl)-1-pyridin-2-ylmethyl-2,3-dihydro-1H-quinolin-4-one

HRID 226939

Reaction equation

HRID 226939 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([CH:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH2:10]1)=[O:8].Br.Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([CH:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 670719673-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one

Product 1

HCID 670721513-(3,4-Dimethyl-benzoyl)-1-pyridin-2-ylmethyl-2,3-dihydro-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4n was prepared following the procedure outlined in Step 3 of Example 1 using 32 mg (0.8 mmol) of sodium hydride (60%), 86 mg (0.31 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3 mL of anhydrous dimethylformamide, and 101.2 mg (0.40 mmol) of 2-bromomethylpyridine hydrobromide. The crude product 4n was purified by flash chromatography to yield 32 mg pale yellow solid (29%): LC-MSD, m/z for C24H20N2O2, [M+H]+=369.4, [M+2H]+=370.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.084 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.32 (d, 6H), 5.50 (s, 2H), 7.1 (d, 1H), 7.2 (d, 1H), 7.25-7.3 (m, 1H), 7.3-7.5 (m, 2H), 7.54-7.62 (m, 2H), 7.62-7.7 (m, 2H), 8.34 (s, 1H), 8.4-8.5 (m, 1H), 8.62 (d, 1H).

Workup

  1. customThe crude product 4n was purified by flash chromatography

Sources & evidence

ORD record
ord-3119c46822ce47d59938a65d603f5a6a
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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