HCID 59191221, compound → HCID 59191315, compound

HRID 1023996Notes

Reaction equation

HRID 1023996 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[F:21])O)=[CH:9][C:8]=1[O:22][CH3:23])(C)(C)C>CO.OS(O)(=O)=O.[Pd]>[F:21][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([OH:6])=[C:8]([O:22][CH3:23])[CH:9]=1

Participants

5

Reactant 1

HCID 59191221HCID 59191221, compound

Product 1

HCID 59191315HCID 59191315, compoundYield 73.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
35 °C

Procedure

Pd/C (0.02 mmol; 40 mg) was added to a solution of [4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-(3-fluoro-pyridin-4-yl)-methanol (0.19 mmol; 70 mg) in methanol (2 mL) and H2SO4 (0.5 mL). The mixture was flushed twice with hydrogen, and the reaction was stirred overnight at 35° C. The mixture was filtered on celite, washed with methanol. After concentration, water was added (3 mL) and K2CO3 until pH 8. The aqueous phase was extracted with ethyl acetate (2*3 mL). Combined organic phases were dried over MgSO4, concentrated to yield the title compound as a white solid (32 mg; 0.14 mmol; 71%) used as such.

Workup

  1. customThe mixture was flushed twice with hydrogen
  2. filtrationThe mixture was filtered on celite
  3. washwashed with methanol
  4. concentrationAfter concentration, water
  5. additionwas added (3 mL) and K2CO3 until pH 8
  6. extractionThe aqueous phase was extracted with ethyl acetate (2*3 mL)
  7. dry with materialCombined organic phases were dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1949cb26381546d491ccc69f1a44177a
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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