m-Chloroperbenzoic acid → 2-[3-(2-Methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol

HRID 1046527

Reaction equation

HRID 1046527 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([OH:21])([CH3:20])[CH3:19])[C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([OH:21])([CH3:19])[CH3:20])[C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1)=[O:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666164252-[3-(2-Methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol

Product 1

HCID 666162852-[3-(2-Methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-olYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol (0.5 g) in DCM (100 mL) was cooled to 0° C., and MCPBA (0.376 g) was added. The reaction mixture was stirred at 0° C. for 2 h, then quenched with 10% Na2S2O3 (aq). The organic layer was washed with NaHCO3 (sat'd aq), separated, and dried over Na2SO4, filtered, concentrated, and titurated with EtOAc and filtered to provide 2-[3-(2-methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol (0.4 g).

Workup

  1. customquenched with 10% Na2S2O3 (aq)
  2. washThe organic layer was washed with NaHCO3 (sat'd aq)
  3. customseparated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationfiltered

Sources & evidence

ORD record
ord-1bf4298c6a04498bb7dbc3c9174139ce
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Linked notes

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