Sodium hydride → HCID 117667378, compound

HRID 712657Notes

Reaction equation

HRID 712657 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 117667378HCID 117667378, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-Bromo-pyridin-3-yl)-methanol (600 mg, 3.2 mmol) in THF (50 mL) is added 60% NaH (160 mg, 3.9 mmol) at 0° C. under N2 atmosphere. The mixture is stirred at room temperature for 1 hour. Then 2-chloro-N,N-dimethyl-acetamide (420 mg, 3.5 mmol) is added into the mixture at 0° C. After addition, the mixture is stirred at room temperature for 16 hrs. After quenching with saturated NH4Cl aqueous solution, the mixture is extracted with EtOAc for three times. The organic layers are combined, dried over Na2SO4, filtered and concentrated. The crude product is purified by preparative TLC to give 700 mg of 2-(5-bromo-pyridin-3-ylmethoxy)-N,N-dimethyl-acetamide.

Workup

  1. additionAfter addition
  2. stirringthe mixture is stirred at room temperature for 16 hrs
  3. customAfter quenching with saturated NH4Cl aqueous solution
  4. extractionthe mixture is extracted with EtOAc for three times
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by preparative TLC

Sources & evidence

ORD record
ord-8c006208b56d476a95b966dd20d45ae8
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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