Sodium hydride → HCID 84311839, compound

HRID 2175273Notes

Reaction equation

HRID 2175273 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:12][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 178515818HCID 178515818, compound

Product 1

HCID 84311839HCID 84311839, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromopyridin-2-ol (0.250 g, 1.437 mmol) in DMF (1.50 mL) at 0° C., was added NaH (60% in mineral oil, 0.075 g, 1.868 mmol) portion-wise over a period of 10 min. The mixture was warmed to room temperature and stirred for 30 min. To the mixture was added methyl 3-(bromomethyl)benzoate (0.395 g, 1.724 mmol) in one portion. The reaction was stirred at room temperature for 16 h and partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (0.274 g, 59% yield) as clear pale-yellow oil. LCMS, [M+H]+=322.0. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=7.7 Hz, 1H), 7.95 (s, 1H), 7.51 (d, J=7.7 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.37 (d, J=2.7 Hz, 1H), 7.33 (dd, J=9.7, 2.7 Hz, 1H), 6.52 (d, J=9.7 Hz, 1H), 5.11 (s, 2H), 3.90 (s, 3H).

Workup

  1. stirringThe reaction was stirred at room temperature for 16 h
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide the crude material
  8. customThe crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b393c30410554b30ad34e6f35b58f8b8
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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