Phosphorus oxychloride → HCID 53212388, compound

HRID 1507418Notes

Reaction equation

HRID 1507418 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[C:7]([C:14]([F:17])([F:16])[F:15])=[N:6]2.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:8]1[C:7]([C:14]([F:17])([F:16])[F:15])=[N:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 491324HCID 491324, compound

Product 1

HCID 53212388HCID 53212388, compoundYield 86%

Conditions

Temperature
140 °C

Procedure

A mixture of 6-methoxy-3-(trifluoromethyl)quinoxalin-2(1H)-one (500 mg, 2.05 mmol) and POCl3 (4 mL) was stirred under microwave at 140° C. for 2 hours. The reaction was quenched with aqueous saturated NaHCO3 (50 mL) and extracted with EtOAc (50 mL×3), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=10/1) to give Intermediate 11 (460 mg, yield 86%). 1H NMR (DMSO-d6 400 MHz): δ 8.10 (d, J=9.6 Hz, 1H), 7.76 (dd, J=9.2, 2.8 Hz, 1H), 7.68 (d, J=2.8 Hz, 1H), 4.01 (s, 3H).

Workup

  1. customThe reaction was quenched with aqueous saturated NaHCO3 (50 mL)
  2. extractionextracted with EtOAc (50 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (PE/EtOAc=10/1)

Sources & evidence

ORD record
ord-ac5f07cb25644347a5e2caae2fefc54d
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

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