Dimethylformamide → 3-(3,4-Dimethyl-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 226948

Reaction equation

HRID 226948 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].[CH3:24][C:25]1C=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br.C[N:34](C)C=O>>[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]([CH2:24][C:25]2[CH:32]=[CH:31][CH:30]=[C:27]([CH3:28])[N:34]=2)[CH:10]=1)=[O:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 670719673-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one

Product 1

HCID 167308563-(3,4-Dimethyl-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Procedure

Compound 4z was prepared following the procedure outlined in Step 3 of Example 1 using 15.6 mg (0.39 mmol) of sodium hydride (60%), 83.2 mg (0.30 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 73.0 mg (0.39 mmol) of 3-methylbenzylbromide. The crude product was purified by flash chromatography to yield 61 mg of a colorless solid 4z: LC-MSD, M/z for C25H22N2O2, [M+H]+=383.4, [M+2H]+=384.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.484 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.32 (d, 6H), 2.58 (s, 3H), 5.42 (s, 2H), 6.83 (d, 1H), 7.08 (d, 1H), 7.16 (d, 1H), 7.36-7.43 (m, 2H), 7.48-7.60 (m, 3H), 7.64 (s, 1H), 8.31 (s, 1H), 8.46 (d, 1H).

Workup

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

Sources & evidence

ORD record
ord-85e8a4d3d13c4ac99f7a2f3b30c252d3
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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