Tetrahydrofuran → 6-(4-Chlorophenyl)-7-(2,4-dichlorophenyl)-2-methyl-2,3-dihydro-4H-pyrano[2,3-b]pyridin-4-one

HRID 1673203Notes

Reaction equation

HRID 1673203 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=[O:15])[C:12]([C:16]#N)=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.C[Mg+].[Br-].[CH:28]([Mg]Br)=[CH:29][CH3:30].C1C[O:36]CC1>>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:10]2[CH:11]=[C:12]3[C:16](=[O:36])[CH2:28][CH:29]([CH3:30])[O:15][C:13]3=[N:14][C:9]=2[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrileHCID 178418689HCID 178418689, compoundHCID 178456053HCID 178456053, compound

Product 1

HCID 250605396-(4-Chlorophenyl)-7-(2,4-dichlorophenyl)-2-methyl-2,3-dihydro-4H-pyrano[2,3-b]pyridin-4-one

Conditions

Temperature
50 °C

Procedure

To the product of Example 1 Step B (7.0 g, 18.6 mmol in THF (90 mL) was added MeMgBr (1.4 M in toluene/THF, 14 mL, 19.6 mmol). After stirring for 3 min, prop-1-enylmagnesium bromide (0.5 M in THF, 55.9 mL, 28 mmol) was added and the temperature was increased to 50° C. The reaction was quenched with 2 M HCl after 30 min and diluted with EtOAc. The solution was washed with brine, and concentrated The residue was purified by flash chromatography on silica gel gradient eluted with 0-35% EtOAc in hexane to afford the title compound. (LC-2) HPLC/MS: 418.2 (M+1), 420.2 (M+3); Rt=4.08 min.

Workup

  1. customThe reaction was quenched with 2 M HCl after 30 min
  2. additiondiluted with EtOAc
  3. washThe solution was washed with brine
  4. concentrationconcentrated The residue
  5. customwas purified by flash chromatography on silica gel gradient
  6. washeluted with 0-35% EtOAc in hexane

Sources & evidence

ORD record
ord-b796778ead8f430181fc6a2b07ccb44b
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

Loading…