Sodium hydride → 2-Bromo-6-{[(1,3-dimethyl-1H-pyrazol-5-yl)methoxy]methyl}pyridine

HRID 385865Notes

Reaction equation

HRID 385865 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]1[N:9]([CH3:10])[N:8]=[C:7]([CH3:11])[CH:6]=1.[Br:12][C:13]1[N:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][CH:14]=1>C1COCC1.O.C(Cl)Cl>[Br:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH2:19][O:20][CH2:4][C:5]2[N:9]([CH3:10])[N:8]=[C:7]([CH3:11])[CH:6]=2)[N:18]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 3517811(6-Bromopyridin-2-yl)methanolHCID 49612705-(chloromethyl)-1,3-dimethyl-1H-pyrazole

Product 1

HCID 595264002-Bromo-6-{[(1,3-dimethyl-1H-pyrazol-5-yl)methoxy]methyl}pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (64 mg, 1.59 mmol) in THF (4 mL) at 0° C. under argon was added 5-(chloromethyl)-1,3-dimethyl-1H-pyrazole (230 mg, 1.59 mmol) and allowed to stir for 20 minutes. (6-Bromopyridin-2-yl)methanol (150 mg, 0.80 mmol) was then added and the mixture was allowed to warm to room temperature and then heated to 55° C. overnight. The reaction was then cooled to ambient temperature and quenched by the addition of water. The quenched reaction mixture was diluted with water (10 mL) and DCM (10 mL) and shaken. The suspensions were passed through disposable phase separators and the DCM eluent was captured and evaporated to dryness to afford the title compound which was used without further purification.

Workup

  1. temperatureheated to 55° C. overnight
  2. temperatureThe reaction was then cooled to ambient temperature
  3. customquenched by the addition of water
  4. customThe quenched reaction mixture
  5. stirringshaken
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1c4f12a47b554e4ca4a1b2448dbb31cb
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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