Triethylamine → 2-[5-(3-Cyanophenyl)-1-benzofuran-2-yl]ethyl methanesulfonate

HRID 494856Notes

Reaction equation

HRID 494856 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])=[CH:9][C:7]=2[CH:8]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:28][S:29]([O:1][CH2:2][CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]3[CH:20]=[CH:19][CH:18]=[C:15]([C:16]#[N:17])[CH:14]=3)=[CH:9][C:7]=2[CH:8]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 114143653-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]benzonitrile

Product 1

HCID 222744452-[5-(3-Cyanophenyl)-1-benzofuran-2-yl]ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 112C (170 mg, 0.65 mmol) and triethylamine (100 μL, 0.72 mmol) were dissolved into CH2Cl2 (3 mL) and cooled to 0° C. The solution was treated with methanesulfonyl chloride (55 μL, 0.71 mmol), and after 10 minutes it was permitted to slowly warm to room temperature. More methanesulfonyl chloride (10 μL, 0.13 mmol) and triethylamine (10 μL, 0.072 mmol) were added. The mixture was stirred until the reaction was nearly complete and then washed consecutively with water and brine, dried (Na2SO4), concentrated, and used without further purification in the next step.

Workup

  1. temperatureto slowly warm to room temperature
  2. washwashed consecutively with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customused without further purification in the next step

Sources & evidence

ORD record
ord-23cb2fec81b44a0399efa54afcdf71fe
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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