Triethylamine → 2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethyl methanesulfonate

HRID 734791Notes

Reaction equation

HRID 734791 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]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:30]=[CH:29][C:24]([O:25][CH2:26][CH2:27][OH:28])=[C:23]([CH3:31])[CH:22]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C>C1COCC1>[CH3:1][S:2]([O:28][CH2:27][CH2:26][O:25][C:24]1[CH:29]=[CH:30][C:21]([C:20]#[C:19][C:16]2[CH:15]=[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:22][C:23]=1[CH3:31])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 673624362-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

Product 1

HCID 865946832-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.74 mL (35.29 mmol) of methanesulfonic acid chloride was added dropwise at 0° C. to a solution of 10.70 g (29.41 mmol) of 2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol and 4.08 mL (29.41 mmol) of triethylamine in 500 mL of THF and the mixture was then stirred for 2 hours at RT. The reaction mixture was filtered and the filtrate was evaporated down in vacuo. The residue was stirred with diethyl ether and water, and the precipitate was filtered off and dried in vacuo. Yield: 11.00 g (85% of theoretical); C23H20ClNO4S (M=441.928); calc.: molpeak (M+H)+: 442/444 (Cl); found: molpeak (M+H)+: 442/444 (Cl); HPLC-MS: 6.36 minutes (method C).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated down in vacuo
  3. stirringThe residue was stirred with diethyl ether and water
  4. filtrationthe precipitate was filtered off
  5. customdried in vacuo
  6. custom6.36 minutes (method C)

Sources & evidence

ORD record
ord-bed4244c144b49cf92a8ebc9703e3a07
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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