Ethyl Acetate → 1-[4-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)phenyl]ethanol

HRID 1678797Notes

Reaction equation

HRID 1678797 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1)=[N:7]2.[CH3:26][Mg]Br.C(OCC)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]([OH:17])[CH3:26])=[CH:14][CH:13]=1)=[N:7]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 575007324-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 594729191-[4-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)phenyl]ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde (9-1, 0.500 g, 1.450 mmol) in anhydrous methylene chloride (10 mL) was added methymagnesium bromide (2.072 mL, 2.9 mmol, 1.4M in toluene/tetrahydrofuran (75:25)) at 0° C. After 15 minutes, the reaction mixture was poured into ethyl acetate, and the organic layer was washed with a saturated solution of sodium bicarbonate, water, then brine, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure gave the title compound. MS (M+H+): calculated=361.85, observed=361.1.

Workup

  1. washthe organic layer was washed with a saturated solution of sodium bicarbonate, water
  2. dry with materialbrine, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-936709ca1a694d0a9193d146c71a4ee0
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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