Triethylamine → HCID 57722725, compound

HRID 1987067Notes

Reaction equation

HRID 1987067 reaction equation
[F:1][C:2]([F:12])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)[CH2:3][OH:4].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C1COCC1>[F:12][C:2]([F:1])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)[CH2:3][O:4][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68827999HCID 68827999, compound

Product 1

HCID 57722725HCID 57722725, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2-difluoro-2-(6-methyl-pyridin-2-yl)-ethanol (2.82 g, 16.3 mmol) (prepared essentially as described in Example 1f) in anhydrous THF (60 mL) at 0° C. was added methanesulfonyl chloride (1.52 mL, 19.6 mmol), followed by triethylamine (4.54 mL, 32.6 mmol). After 2.5 hours, the reaction mixture was quenched with ice/water. The resulting mixture was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and evaporated to afford the desired product as a clear oil (3.7 g, 97%). 1H NMR (CDCl3) δ 7.73 (t, J=7.77 Hz, 1H), 7.51 (d, J=7.75 Hz, 1H), 7.28 (d, J=8.04 Hz, 1H), 4.89 (t, J=12.88 Hz, 2H), 3.07 (s, 3H), 2.58 (s, 3H); LC/MS (m/z) [M+1] 252.2 (calculated for C9H12F2NO3S, 252.0).

Workup

  1. customat 0° C.
  2. customthe reaction mixture was quenched with ice/water
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-1446d30fdcb940eb84b320443889ff75
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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