Water → HCID 57885697, compound

HRID 1521592Notes

Reaction equation

HRID 1521592 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[N:8][CH:9]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].O>O1CCCC1>[CH3:12][S:13]([O:11][CH2:10][C:6]1[CH:7]=[N:8][CH:9]=[C:4]([Br:3])[CH:5]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 57885697HCID 57885697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) suspension of sodium hydride (60% dispersion in mineral oil, 0.064 g, 1.60 mmol) in tetrahydrofuran (5 mL) was added a solution of (5-bromopyridin-3-yl)methanol (0.200 g, 1.06 mmol) in tetrahydrofuran (5 mL). After stirring for 1 hour, methanesulfonyl chloride (0.099 mL, 1.28 mmol) was added. The reaction was then warmed to room temperature and stirred until complete. The reaction was then poured into water and extracted with ethyl acetate. The organic extracts were combined, washed with water and saturated aqueous sodium chloride solution, dried, filtered, and concentrated under reduced pressure to provide the title compound: LCMS m/z 267.86 [M+2+H]+.

Workup

  1. temperatureTo a cooled
  2. stirringstirred until complete
  3. extractionextracted with ethyl acetate
  4. washwashed with water and saturated aqueous sodium chloride solution
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6df225e49ea14472b0d6b8de5c956216
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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