Water → 2-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfonyl)pyridine

HRID 1882123Notes

Reaction equation

HRID 1882123 reaction equation
[CH3:1][C:2]([C:21]1[CH:26]=[CH:25][C:24](SC)=[CH:23][N:22]=1)([C:10]1[NH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:13][CH:14]=1)[CH2:3][CH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.O1CCC[CH2:30]1.O.O[O:36][S:37]([O-:39])=O.[K+]>C(OCC)(=O)C.CO>[CH3:1][C:2]([C:21]1[CH:26]=[CH:25][C:24]([S:37]([CH3:30])(=[O:39])=[O:36])=[CH:23][N:22]=1)([C:10]1[NH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:13][CH:14]=1)[CH2:3][CH:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 593312412-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine

Product 1

HCID 593315142-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfonyl)pyridineYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine (84.0 mg), tetrahydrofuran (1 mL), water (1 mL) and methanol (1 mL) was added Oxone (registered trademark) (157 mg), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (55.5 mg, yield 61%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). melting point 135-136° C. MS: 426 (MH+).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1961fb1847f742b99b40b91e26933feb
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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