Triethylamine → 2-{4-[5-(4-Chlorophenyl)-3-fluoropyridin-2-ylethynyl]phenoxy}ethyl methanesulfonate

HRID 734802Notes

Reaction equation

HRID 734802 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]([F:31])[C:16]([C:19]#[C:20][C:21]3[CH:30]=[CH:29][C:24]([O:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:22]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:28][CH2:27][CH2:26][O:25][C:24]1[CH:23]=[CH:22][C:21]([C:20]#[C:19][C:16]2[C:15]([F:31])=[CH:14][C:13]([C:10]3[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=3)=[CH:18][N:17]=2)=[CH:30][CH:29]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 690591092-{4-[5-(4-Chlorophenyl)-3-fluoropyridin-2-ylethynyl]phenoxy}ethanol

Product 1

HCID 866011332-{4-[5-(4-Chlorophenyl)-3-fluoropyridin-2-ylethynyl]phenoxy}ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 63 μL (0.816 mmol) of methanesulfonyl chloride was added dropwise to a solution of 0.20 g (0.544 mmol) of 2-{4-[5-(4-chlorophenyl)-3-fluoropyridin-2-ylethynyl]phenoxy}ethanol and 0.11 mL (0.816 mmol) of triethylamine in 10 mL of DCM and the mixture was stirred for 16 hours at RT. A further 0.11 mL (0.816 mmol) of triethylamine and 63 μL (0.816 mmol) of methanesulfonyl chloride were added and the mixture was stirred for 8 hours. The reaction mixture was diluted with DCM, and the organic phase was washed with water and dilute aqueous sodium bicarbonate solution, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 0.24 g (99% of theoretical); C22H17ClFNO4S (M=445.892); calc.: molpeak (M+H)+: 446/448 (Cl); found: molpeak (M+H)+: 446/448 (Cl); HPLC-MS: 6.19 minutes (method B).

Workup

  1. stirringthe mixture was stirred for 8 hours
  2. washthe organic phase was washed with water and dilute aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down in vacuo
  5. custom6.19 minutes (method B)

Sources & evidence

ORD record
ord-5a601ce0443b43d99e7d5b790132f340
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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