Triethylamine → HCID 86691607, compound

HRID 522608Notes

Reaction equation

HRID 522608 reaction equation
[F:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][S:19]([O:10][CH2:9][C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][N:4]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53414314(3,5-Difluoropyridin-2-YL)methanol2×

Product 1

HCID 86691607HCID 86691607, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Intermediate 9 (3,5-difluoro-2-pyridinyl)methanol (114 mg, 0.786 mmol) was dissolved in DCM (anh) (6 mL) at 0° C. N,N-diethylethanamine (ALDRICH, 0.131 mL, 0.943 mmol) and methanesulfonyl chloride (ALDRICH, 0.067 mL, 0.864 mmol) were added. Reaction mixture was stirred at 0° C. for 1 h 30 min. Crude of reaction was partitioned between water and DCM, aqueous layer was extracted with DCM (2×10 mL). Organic layers were dried over MgSO4 (anh) and filtered. Solvent was eliminated to yield title compound (3,5-difluoro-2-pyridinyl)methyl methanesulfonate (137 mg, 0.614 mmol, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm: 1H NMR (300 MHz, DMSO-d6) δ ppm: 8.58 (d, 1H), 8.06-8.11 (m, 1H), 5.36 (d, 2H), 3.27 (s, 3H). [ES+MS] m/z 224 (MH+).

Workup

  1. customReaction mixture
  2. customCrude of reaction
  3. customwas partitioned between water and DCM, aqueous layer
  4. extractionwas extracted with DCM (2×10 mL)
  5. dry with materialOrganic layers were dried over MgSO4 (anh)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-dfc72f13a98f499ea784d5e17fbff2b4
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

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