Sodium hydride → 3-Bromo-5-(3-methanesulfonyl-propoxymethyl)-pyridine

HRID 712646Notes

Reaction equation

HRID 712646 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][OH:8])(=[O:4])=[O:3].[H-].[Na+].[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18]Br)[CH:17]=1.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O.O>[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][O:8][CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2004243-(Methylsulfonyl)-1-propanolHCID 149329483-Bromo-5-(bromomethyl)pyridine

Product 1

HCID 1176674223-Bromo-5-(3-methanesulfonyl-propoxymethyl)-pyridineYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methanesulfonyl-propan-1-ol (69 mg, 0.50 mmol) is dissolved in 2.0 mL of DMF and 60% sodium hydride (20 mg, 0.50 mmol) is added at 0° C. The mixture is stirred for 15 min and 3-bromo-5-bromomethyl-pyridine (50 mg, 0.20 mmol) is added. The mixture is stirred for 2 hrs and saturated aqueous NH4Cl solution (3 mL) is added along with water (10 mL) and EtOAc (10 mL). The mixture is stirred for 10 min and the aqueous layer is separated and extracted with EtOAc (2×15 ml). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 61 mg of 3-bromo-5-(3-methanesulfonyl-propoxymethyl)-pyridine.

Workup

  1. stirringThe mixture is stirred for 2 hrs
  2. stirringThe mixture is stirred for 10 min
  3. customthe aqueous layer is separated
  4. extractionextracted with EtOAc (2×15 ml)
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-ad44a76cf9a24adb888cb67d40b49d5f
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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