Sodium hydride → 7-(4-Chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one

HRID 14462Notes

Reaction equation

HRID 14462 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12](F)[C:13]([NH:19][CH2:20][CH2:21][OH:22])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:24]([CH3:26])[CH3:25])=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]4[C:13](=[CH:14][CH:15]=3)[NH:19][CH2:20][CH2:21][O:22]4)[O:10][C:9]=2[CH:24]([CH3:26])[CH3:25])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 687043963-(4-Chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one

Product 1

HCID 167498117-(4-Chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one (0.195 g, 0.52 mmol) in dimethylformamide (5 ml) is added sodium hydride (0.053 g, 1.32 mmol, 60% dispersion in mineral oil, 2.55 eq.). The mixture is irradiated in a microwave instrument at 150° C. for 70 min. The solvent is removed by evaporation in vacuo to afford a brown oil. This is dissolved in hot ethyl acetate and allowed to cool to room temperature, whereupon a brown solid precipitates. More product can be recovered from the mother liquor by flash chromatography (cyclohexane/ethyl acetate=9:1). The solid products are combined and dried at 60° C. overnight under high vacuum to afford the title compound.

Workup

  1. customThe mixture is irradiated in a microwave instrument at 150° C. for 70 min
  2. customThe solvent is removed by evaporation in vacuo
  3. customto afford a brown oil
  4. customprecipitates
  5. customMore product can be recovered from the mother liquor by flash chromatography (cyclohexane/ethyl acetate=9:1)
  6. customdried at 60° C. overnight under high vacuum

Sources & evidence

ORD record
ord-9d7bc16263144da7a3749d7bd775db3b
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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