Dimethyl Sulfoxide → HCID 89955073, compound

HRID 705349

Reaction equation

HRID 705349 reaction equation
[C:1]([C:3]1[C:7]2[CH:8]=[C:9]([CH:17]3[CH2:19][CH2:18]3)[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:6]=2[O:5][C:4]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:34][CH2:35][CH2:36][CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].CS(C)=O>C(#N)C>[Si:39]([O:38][CH2:37][CH2:36][CH2:35][CH2:34][N:12]([C:10]1[C:9]([CH:17]2[CH2:18][CH2:19]2)=[CH:8][C:7]2[C:3]([C:1]#[N:2])=[C:4]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[O:5][C:6]=2[CH:11]=1)[S:13]([CH3:16])(=[O:15])=[O:14])([C:42]([CH3:43])([CH3:44])[CH3:45])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 89955206N-[3-cyano-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl]methanesulfonamide

Product 1

HCID 89955073HCID 89955073, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of Example 11A (0.1302 g, 0.352 mmol) and potassium carbonate (0.058 g, 0.422 mmol) in acetonitrile (2 mL) was heated at reflux for 30 minutes, then (4-iodobutoxy)-tert-butyldimethylsilane (0.122 g, 0.387 mmol) was added and the resultant mixture was stirred at reflux for 0.5 hour. The reaction mixture became thick so additional acetonitrile (2 mL) and dimethyl sulfoxide (2 mL) were added, and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo to a yellow oil that was taken up in ethyl acetate (100 mL) and washed with 1 N aqueous H3PO4, 10% aqueous NaHCO3, and 10% aqueous NaCl. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo leaving a yellow oil. Purification on a silica gel column (12 g) eluting with a gradient of 10/90 ethyl acetate/hexane to 50/50 ethyl acetate/hexane over 20 minutes afforded the title compound (0.135 g, 69%).

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureat reflux for 0.5 hour
  3. additionwere added
  4. concentrationThe reaction mixture was concentrated in vacuo to a yellow oil that
  5. washwashed with 1 N aqueous H3PO4, 10% aqueous NaHCO3, and 10% aqueous NaCl
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customleaving a yellow oil
  10. customPurification on a silica gel column (12 g)
  11. washeluting with a gradient of 10/90 ethyl acetate/hexane to 50/50 ethyl acetate/hexane over 20 minutes

Sources & evidence

ORD record
ord-cd9e9a774bb1432d824d84ce45d9b8f7
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Linked notes

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