3-Hydroxypyridine → HCID 24963792, compound

HRID 1160203Notes

Reaction equation

HRID 1160203 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:9][C:10]1[CH:28]=[CH:27][C:13]([CH2:14][N:15]2[CH2:19][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:16]2=[O:26])=[CH:12][CH:11]=1.[H-].[Na+]>CN(C=O)C.ClCCl>[C:20]1([C@H:18]2[O:17][C:16](=[O:26])[N:15]([CH2:14][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][O:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)=[CH:28][CH:27]=3)[CH2:19]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 24963437HCID 24963437, compound

Product 1

HCID 24963792HCID 24963792, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-hydroxypyridine (23 mg, 0.24 mmol) in DMF (1 mL) was added to a suspension of 3-(4-bromomethyl-benzyl)-5-(R)-phenyl-oxazolidin-2-one (70 mg, 0.20 mmol) (synthesized according to procedure 4) and sodium hydride (60%) (9 mg, 0.22 mmol) in DMF (1.5 mL) and the reaction mixture was stirred overnight at RT. It was diluted with dichloromethane (6 mL), washed with water (2×5 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by chromatography on silica gel, eluting with dichloromethane containing 0.25-1% of methyl alcohol, to yield the title compound as a white solid (33 mg, 45%). 1H NMR (300 MHz, CDCl3): δ 8.40 (s, 1H), 8.25 (s, 1H), 7.38 (m, 1H), 5.50 (dd, 1H), 5.11 (s, 2H), 4.59 (d, 1H), 4.43 (d, 1H), 3.80 (t, 1H), 3.34 (dd, 1H).

Workup

  1. washwashed with water (2×5 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by chromatography on silica gel
  5. washeluting with dichloromethane containing 0.25-1% of methyl alcohol

Sources & evidence

ORD record
ord-9c80dbd7c13f4e0fbec204a79b16dab0
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

Loading…