Cesium carbonate → HCID 25234309, compound

HRID 1665059Notes

Reaction equation

HRID 1665059 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([CH2:16][NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])(=[O:20])=[O:19])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:37](Cl)[CH:38]1[O:42][CH2:41][CH2:40][CH2:39]1>CN(C)C(=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([CH2:16][N:17]([CH2:37][CH:38]3[CH2:39][CH2:40][CH2:41][O:42]3)[S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:28])[F:29])(=[O:20])=[O:19])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 181502-Chloromethyl tetrahydrofuran2×HCID 67440497N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide

Product 1

HCID 25234309HCID 25234309, compoundYield 60.5%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (example 27, step 1, 52 mg) in N,N-dimethylacetamide (0.9 mL) were added cesium carbonate (54 mg), tetrahydrofurfuryl chloride (20 mg) and tetrabutylammonium iodide (4 mg). The mixture was stirred for 3 days at r.t. and for 1 day at 50° C. Tetrahydrofurfuryl chloride (20 mg) was added and the mixture was heated to 100° C. in the microwave oven for 10 min. The mixture was diluted with ethyl acetate and washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 95:5 to 1:1) to give N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-N-(tetrahydro-furan-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (37 mg) as a light yellow oil. MS: 576.7 ([M+NH4]+)

Workup

  1. temperaturethe mixture was heated to 100° C. in the microwave oven for 10 min
  2. washwashed with water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 95:5 to 1:1)

Sources & evidence

ORD record
ord-8ac3af6a965c4a1e96a1b28b8fa35999
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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