Iodoethane → HCID 66788563, compound

HRID 1045641Notes

Reaction equation

HRID 1045641 reaction equation
[CH3:1][CH2:2]C([O-])(C)C.[K+].[CH2:8]([O:10][C:11]([C:13]1[C:18]([CH2:19][S:20]([CH2:23][C:24]2[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:34])(=[O:22])=[O:21])=[N:17][CH:16]=[CH:15][N:14]=1)=[O:12])[CH3:9].ICC>CN(C)C=O>[CH2:8]([O:10][C:11]([C:13]1[C:18]([CH:19]([S:20]([CH2:23][C:24]2[C:29]([C:30]([F:32])([F:31])[F:33])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:34])(=[O:21])=[O:22])[CH2:1][CH3:2])=[N:17][CH:16]=[CH:15][N:14]=1)=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 23683543Potassium t-amylateHCID 66789121HCID 66789121, compound

Product 1

HCID 66788563HCID 66788563, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-pentoxide (0.155 ml, ˜1.7M solution in toluene, Aldrich 60435) was added drop wise to a cooled (0 to 5° C.) solution of 3-(2-chloro-6-trifluoromethyl-phenylmethanesulfonylmethyl)-pyrazine-2-carboxylic acid ethyl ester (Compound B13 of Table B) (0.1 g) in N,N-dimethylformamide (1 ml) under nitrogen atmosphere and stirred cold for 20 minutes. Iodoethane (0.021 ml) was added to the cool dark red solution and stirred at this temperature for a further hour. The reaction mixture was partitioned between ether and 2M aqueous hydrochloric acid. The aqueous layer was extracted with further diethyl ether. The combined organic layers were washed further with water and brine, dried over magnesium sulfate and concentrated to give 3-[1-(2-chloro-6-trifluoromethyl-phenylmethanesulfonyl)-propyl]-pyrazine-2-carboxylic acid ethyl ester Compound No. D1 of Table D (0.106 g). MH+=451, RT=1.58 min.

Workup

  1. stirringstirred at this temperature for a further hour
  2. customThe reaction mixture was partitioned between ether and 2M aqueous hydrochloric acid
  3. extractionThe aqueous layer was extracted with further diethyl ether
  4. washThe combined organic layers were washed further with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dbff5ec855374a17ab5af4d86c005b48
Source dataset
uspto-grants-2013_10
Patent number
US08569301B2

Reaction notes

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