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

HRID 226941Notes

Reaction equation

HRID 226941 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.BrC[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.[CH3:33]N(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]([CH2:33][C:32]2[CH:31]=[N:30][CH:29]=[CH:28][CH:27]=2)[CH2:10]1)=[O:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 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-one

Procedure

Compound 4p 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 4-bromomethylpyridine hydrobromide. The crude product was purified by flash chromatography to yield 27 mg of yellowish solid 4p: 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=1.334 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 5.4 (s, 2H), 7.10 (d, 1H), 7.16-7.22 (m, 2H), 7.42 (t, 1H), 7.52-7.66 (m, 3H), 8.26 (d, 1H), 8.48 (m, 1H), 8.58-8.64 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-48765248fae449969259d024b9f00b2e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…