Cesium carbonate → HCID 25234253, compound

HRID 1665057Notes

Reaction equation

HRID 1665057 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+].Br[CH2:38][CH:39]1[O:43][CH2:42][CH2:41][O:40]1>CN(C)C(=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[O:40]1[CH2:41][CH2:42][O:43][CH:39]1[CH2:38][N:17]([CH2:16][C:14]1[S:15][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=2)=[CH:12][CH:13]=1)[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([F:30])([F:28])[F:29])(=[O:20])=[O:19]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 780681,3-Dioxolane, 2-(bromomethyl)-3×HCID 67440497HCID 67440497, compound

Product 1

HCID 25234253HCID 25234253, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalyst2×HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (example 27, step 1, 44 mg) in N,N-dimethylacetamide (0.8 mL) were added cesium carbonate (45 mg), 2-bromomethyl-1,3-dioxolane (23 mg) and tetrabutylammonium iodide (3 mg). The mixture was stirred for 3 days at r.t. More tetrabutylammonium iodide (3 mg) and 2-bromomethyl-1,3-dioxolane (23 mg) were added and the mixture was stirred for 18 h at r.t. and for 24 h at 50° C. 2-Bromomethyl-1,3-dioxolane (23 mg) was added and the mixture was stirred for 5 h at 100° C. 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 9:1 to 1:1) to give N-[1,3]dioxolan-2-ylmethyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (34 mg) as a light yellow oil. MS: 578.6 ([M+NH4]+)

Workup

  1. stirringthe mixture was stirred for 18 h at r.t. and for 24 h at 50° C
  2. stirringthe mixture was stirred for 5 h at 100° C
  3. washwashed with water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 9:1 to 1:1)

Sources & evidence

ORD record
ord-40703128a8ce48a581599cb3efea77e6
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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