Sodium hydride → HCID 117667291, compound

HRID 712736Notes

Reaction equation

HRID 712736 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C1COCC1>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:9][CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 117667291HCID 117667291, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5-Bromo-pyridin-3-yl)-methanol (25.0 g, 0.13 mol) is added to a solution of NaH (6.45 g, 0.27 mol) in THF (500 ml) at 0° C. and stirred at room temperature for 30 min. Benzyl bromoacetate (34.4 g, 0.15 mol) is added to this solution at 0° C. and stirred at room temperature overnight. The mixture is quenched with water and diluted with DCM. The organic layer is dried over Na2SO4 and concentrated in vacuo. The product is chromatographed on silica gel to give (5-bromo-pyridin-3-ylmethoxy)-acetic acid benzyl ester (10 g).

Workup

  1. stirringstirred at room temperature overnight
  2. customThe mixture is quenched with water
  3. additiondiluted with DCM
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe product is chromatographed on silica gel

Sources & evidence

ORD record
ord-28f1b2b07d534fa2a53750da408aeb18
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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