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

HRID 226940Notes

Reaction equation

HRID 226940 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)=[O:8].Br.Br[CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=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:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 669006323-(3,4-Dimethyl-benzoyl)-1-pyridin-3-ylmethyl-2,3-dihydro-1H-quinolin-4-oneYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4o 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 3a, 3 mL of anhydrous dimethylformamide, and 101.2 mg (0.40 mmol) of 3-bromomethylpyridine hydrobromide. The crude product was purified by flash chromatography to yield 29 mg of pale yellow solid 4o: 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=1.436 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 5.4 (s, 2H), 7.17 (d, 1H), 7.26-7.32 (m, 2H), 7.40 (t, 1H), 7.52-7.64 (m, 3H), 8.27 (s, 1H), 8.46 (d, 1H), 8.58-8.64 (m, 2H).

Workup

  1. customCompound 4o was prepared
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-60499b08c5824e61ba983783b639a44e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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