Dimethylformamide → 3-(3,4-Dimethyl-benzoyl)-1-(3-fluoro-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 226957Notes

Reaction equation

HRID 226957 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].CN(C)C=O.Br[CH2:30][C:31]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][N:32]=1>C(#N)C>[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)[N:11]([CH2:30][C:31]2[C:36]([F:37])=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:10]=1)=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 216131732-(Bromomethyl)-3-fluoropyridineHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 167310123-(3,4-Dimethyl-benzoyl)-1-(3-fluoro-pyridin-2-ylmethyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 4ll was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 138.6 mg (0.50 mmol) of 3-(3,4-Dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a, 3 mL of anhydrous dimethylformamide, and 123.5 mg (0.65 mmol) of 2-bromomethyl-3-fluoro-pyridine. The crude product was purified by flash chromatography to yield 96 mg of 4ll as a colorless solid: LC-MSD, m/z for C24H19FN2O2, [M+H]+=387.5, [M+2H]+=388.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.192 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 5.56 (s, 2H), 7.17 (d, 1H), 7.31 (m, 1H), 7.38 (t, 1H), 7.46 (t, 1H), 7.56-7.70 (m, 4H), 8.35-8.42 (m, 2H), 8.42-8.47 (m, 1H).

Workup

  1. customCompound 4ll was prepared
  2. customThe crude product was purified by flash chromatography
  3. customto yield 96 mg of 4ll as a colorless solid

Sources & evidence

ORD record
ord-50daf4c08994474f93f93737393fcae9
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…