Triphenylphosphine → 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-quinoxaline-2,3-dione

HRID 1025828Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8](O)[C:7](=[O:14])[C:6](=[O:15])[N:5]2[CH:16]1[CH2:18][CH2:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:8][C:7](=[O:14])[C:6](=[O:15])[N:5]2[CH:16]2[CH2:18][CH2:17]2)=[CH:10][C:11]=1[F:12]

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 685 mg (2.531 mmol) 6-chloro-4-cyclopropyl-7-fluoro-1-hydroxy-1,4-dihydro-quinoxaline-2,3-dione in 10 mL N,N-dimethylformamide was added 996 mg (3.796 mmol) triphenylphosphine. The reaction mixture was stirred for 4 hours at 135° C. The reaction mixture was concentrated under vacuum (15 mbar/55° C.). The residue was suspended in 20 mL dichloromethane. The suspension was stirred for 30 min at 0° C. and filtered and washed with 20 mL dichloromethane. White solid (63%). MS (ESI): m/z=255.034 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under vacuum (15 mbar/55° C.)
stirringThe suspension was stirred for 30 min at 0° C.
filtrationfiltered
washwashed with 20 mL dichloromethane

Sources & evidence

ORD record: ord-7e1ac52abe444e49b1e14c5e66b8f14f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729091B2

Reaction notes

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