Methanol → 1-[6-(5-{1-[3-fluoro-4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1882008Notes

Reaction equation

HRID 1882008 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]([C:18]2[NH:22][C:21]([C:23]3[N:28]=[CH:27][C:26]([CH:29]([OH:32])[CH2:30][OH:31])=[CH:25][CH:24]=3)=[CH:20][CH:19]=2)[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1SC.O1CCC[CH2:34]1.CO.O[O:41][S:42]([O-:44])=O.[K+]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]([C:18]2[NH:22][C:21]([C:23]3[N:28]=[CH:27][C:26]([CH:29]([OH:32])[CH2:30][OH:31])=[CH:25][CH:24]=3)=[CH:20][CH:19]=2)[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[S:42]([CH3:34])(=[O:44])=[O:41]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 593313981-[6-(5-{1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

Product 1

HCID 593315531-[6-(5-{1-[3-fluoro-4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diolYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-[6-(5-{1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol (367 mg) in a mixed solvent of tetrahydrofuran (3 mL), methanol (3 mL) and water (3 mL) was added Oxone (registered trademark) (593 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (330 mg, 84%) as a pale-yellow amorphous solid. MS: 489 (MH+).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-71305c37c1504839b000fd1a9cd01ddd
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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