Methanol → HCID 59331352, compound

HRID 1882110Notes

Reaction equation

HRID 1882110 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH:9]1([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([C:29]3[NH:33][C:32]([C:34]4[N:39]=[CH:38][C:37]([CH:40]=[O:41])=[CH:36][CH:35]=4)=[CH:31][CH:30]=3)[CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:11][CH2:10]1.[CH3:42][O-:43].[Na+].[Cl-].[NH4+].[CH3:47]O>CS(C)=O.O>[CH:9]1([S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH:21]([C:29]3[NH:33][C:32]([C:34]4[N:39]=[CH:38][C:37]([CH:40]([O:41][CH3:47])[CH2:42][OH:43])=[CH:36][CH:35]=4)=[CH:31][CH:30]=3)[CH2:22][CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH2:11][CH2:10]1

Participants

9

Reactant 6

HCID 887MethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10942334Sodium MethoxideHCID 593314196-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehyde

Product 1

HCID 59331352HCID 59331352, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a solution of trimethylsulfoxonium iodide (947 mg) in dimethylsulfoxide (5 mL) was added sodium hydride (oil, about 60%) (129 mg) and the mixture was stirred at room temperature m for 1 hr. The reaction mixture was added dropwise to a solution of 6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehyde (1 g) in dimethylsulfoxide (5 mL) and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a crude product (1.0 g). The obtained crude product was dissolved in methanol (10 mL), sodium methoxide (64 mg) was added at room temperature, and the mixture was stirred for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give a pale-yellow amorphous solid from a fraction eluted with ethyl acetate. The obtained pale-yellow amorphous solid was purified by preparative HPLC to give the title compound (310 mg, yield 28%) as a colorless amorphous solid. MS: 511 (MH+).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a crude product (1.0 g)
  7. customThe obtained crude product
  8. stirringthe mixture was stirred for 2 hr
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. customto give a pale-yellow amorphous solid from a fraction
  14. washeluted with ethyl acetate
  15. customThe obtained pale-yellow amorphous solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-ef5a259754064e65a22084ac574f00c4
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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