Triethylamine → 2-Fluoro-5-(methylsulfonylmethyl)pyridine

HRID 556685Notes

Reaction equation

HRID 556685 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22663702(6-Fluoropyridin-3-yl)methanol

Product 1

HCID 666607872-Fluoro-5-(methylsulfonylmethyl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(6-Fluoropyridin-3-yl)methanol (215 mg, 1.69 mmol) in CH2Cl2 (10 mL) containing triethylamine (354 μL, 2.54 mmol) was treated with methanesulfonyl chloride (291 mg, 2.54 mmol) dropwise at 0° C., stirred at 0° C. for 30 min, diluted with water, and extracted with CH2Cl2 (2×10 mL). The combined organic extract was dried (MgSO4), filtered, and concentrated to afford a crude oil.

Workup

  1. extractionextracted with CH2Cl2 (2×10 mL)
  2. extractionThe combined organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a crude oil

Sources & evidence

ORD record
ord-0bf8e227738645389d42e8e9332735a8
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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