Sodium hydride → HCID 86712592, compound

HRID 2175271Notes

Reaction equation

HRID 2175271 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=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[N:7]=[CH:6][C:5]([O:8][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:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 86712592HCID 86712592, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromopyridin-3-ol (0.500 g, 2.87 mmol) in DMF (3.0 mL) at 0° C. was added NaH (60% in mineral oil, 0.149 g, 3.74 mmol) portion-wise over a period of 10 min. The mixture was warmed to room temperature, stirred for 30 min, and methyl 3-(bromomethyl)benzoate (0.790 g, 3.45 mmol) was added in one portion. The reaction was stirred at room temperature for 16 h. The mixture was partitioned between EtOAc and water. The organic layer was separated, 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 (0.726 g, 78% yield) as an off-white solid. LCMS, [M+H]+=322.0.

Workup

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

Sources & evidence

ORD record
ord-8ab57d9d7648480d91833037a8fc9557
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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