Tetrahydrofuran → HCID 59631288, compound

HRID 1431654Notes

Reaction equation

HRID 1431654 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:15]=[C:16]([C:22](=[O:24])[CH3:23])[CH:17]=[CH:18][C:19]=2SC)[C:3]=1[CH3:25].[CH2:26]1COCC1.O[O:32][S:33]([O-:35])=O.[K+]>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:15]=[C:16]([C:22](=[O:24])[CH3:23])[CH:17]=[CH:18][C:19]=2[S:33]([CH3:26])(=[O:35])=[O:32])[C:3]=1[CH3:25]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23707502Potassium hydroxy sulfite2×HCID 59631111HCID 59631111, compound

Product 1

HCID 59631288HCID 59631288, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

The 1-(3-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-4-(methylthio)phenyl)-ethanone (230 mg, 0.61 mmol) was added to a mixture of THF (4.6 mL) and water (1.5 mL). To the milky solution was added Oxone™ (940 mg, 1.5 mmol) and the reaction was stirred for 2.5 days. Another portion of Oxone™ (940 mg, 1.5 mmol) was added along with the same amount of THF and water amounts as initially. The slurry was stirred vigorously overnight. The reaction was then poured into water and stirred vigorously for 10 min. The mixture was filtered and washed with water. The precipitate was dissolved in EtOAc and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica gel, 0 to 100% EtOAc:hexanes) to give 1-(3-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-4-(methylsulfonyl)phenyl)ethanone. Mass Spectrum (ESI) m/e=410.0 (M+1).

Workup

  1. stirringThe slurry was stirred vigorously overnight
  2. stirringstirred vigorously for 10 min
  3. filtrationThe mixture was filtered
  4. washwashed with water
  5. dissolutionThe precipitate was dissolved in EtOAc
  6. dry with materialdried over magnesium sulfate
  7. customThe crude product was purified by medium pressure chromatography (silica gel, 0 to 100% EtOAc:hexanes)

Sources & evidence

ORD record
ord-d001859e9ac8409f9a688122d37edf2c
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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