Hydrogen Peroxide → HCID 54591945, compound

HRID 2276759Notes

Reaction equation

HRID 2276759 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][NH:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:22].[K+].[K+].OO>CS(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][NH:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]([NH2:16])=[O:22])=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 54591943HCID 54591943, compound

Product 1

HCID 54591945HCID 54591945, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) suspension of 6-(2-(4-fluorophenyl)-2-methylpropylamino)nicotinonitrile (75 mg, 0.28 mmol, 1.0 equiv) and K2CO3 (50 mg, 0.36 mmol, 1.3 equiv) in DMSO (1 mL) was added aq. H2O2 (250 uL, 30% by wt., 2.6 mmol, 9 equiv) by syringe. The reaction was allowed to warm to RT and stirred for 30 minutes. The resulting mixture was diluted with EtOAc and washed three times with satd. aq. LiCl and once with brine. The resulting solution was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel chromatography (2%-10% MeOH/DCM) provided the title compound as an off-white foam (54 mg, 77%), (m/z [M+H]=288.1).

Workup

  1. temperatureTo a cooled
  2. washwashed three times with satd
  3. dry with materialThe resulting solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (2%-10% MeOH/DCM)

Sources & evidence

ORD record
ord-a9d7fcb30f3b47ba9d83b6e447a73242
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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