Methanol → 5-Bromo-3-(2-(methylsulfonyl)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1529327Notes

Reaction equation

HRID 1529327 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2[C:17]1[CH:22]=[CH:21][N:20]=[C:19](SC)[N:18]=1.O[O:26][S:27]([O-:29])=O.[K+].[CH3:31]O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:27]([CH3:31])(=[O:29])=[O:26])[N:18]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 679597215-Bromo-3-(2-(methylthio)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 679597205-Bromo-3-(2-(methylsulfonyl)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Procedure

To a RT slurry of 5-bromo-3-(2-(methylthio)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.855 g, 2.109 mmol) in MeOH (40 mL) was added oxone, monopersulfate compound (6.46 g, 10.51 mmol, Aldrich) and the reaction was stirred overnight. The reaction mixture was concentrated to ˜50% volume and diluted with water. The slurry was neutralized with 5 N NaOH and the solids were filtered, washed consecutively with water and MeOH, and dried in vacuo to give 795 mg of a light-yellow amorphous solid. m/z: 437.9, 439.0 [M+1].

Workup

  1. concentrationThe reaction mixture was concentrated to ˜50% volume
  2. additiondiluted with water
  3. filtrationthe solids were filtered
  4. washwashed consecutively with water and MeOH
  5. customdried in vacuo

Sources & evidence

ORD record
ord-11eabbd11d34485eb77f4dd69e413a77
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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