HCID 57425669, compound → HCID 11646200, compound

HRID 1360115Notes

Reaction equation

HRID 1360115 reaction equation
[N:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[N:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[OH:9])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 57425669HCID 57425669, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 11646200HCID 11646200, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-Morpholin-4-yl-2-phenyl-1-pyridin-2-yl-ethanone (15 mg, 0.053 mmol) was dissolved in 3 mL of dry THF and cooled to −78° C. Phenylmagnesium bromide (159 μL, 1.0 M solution in TBH, 0.159 mmol) was added dropwise and the mixture was allowed to stir for 15 minutes. The reaction was quenched with 1 mL of aqueous NaHCO3(sat) and warmed to ambient temperature. The mixture was poured into NaHCO3 (sat) and extracted 2× with EtOAc. The combined organic extracts were dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC. The appropriate fractions were poured into NaHCO3(sat) and extracted 2× with EtOAc. The combined organic extracts were dried with Na2SO4, filtered and concentrated in vacuo to provide the titled compound.

Workup

  1. customThe reaction was quenched with 1 mL of aqueous NaHCO3(sat)
  2. temperaturewarmed to ambient temperature
  3. additionThe mixture was poured into NaHCO3 (sat)
  4. extractionextracted 2× with EtOAc
  5. dry with materialThe combined organic extracts were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative HPLC
  9. additionThe appropriate fractions were poured into NaHCO3(sat)
  10. extractionextracted 2× with EtOAc
  11. dry with materialThe combined organic extracts were dried with Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eda897c3669d4bc89d9c98cb4ef58a8e
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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