Cesium fluoride → (E)4-(2-Cyclohexyl-1-hydroxymethyl-vinyl)-N-methyl-benzenesulfonamide

HRID 2103638Notes

Reaction equation

HRID 2103638 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:13]1(/[CH:19]=[C:20](\B2OC(C)(C)C(C)(C)O2)/[CH2:21][OH:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[F-].[Cs+]>C1COCC1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:13]1(/[CH:19]=[C:20](\[C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=2)/[CH2:21][OH:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 1012154-bromo-N-methylbenzene-1-sulfonamideHCID 67084598(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67084447(E)4-(2-Cyclohexyl-1-hydroxymethyl-vinyl)-N-methyl-benzenesulfonamideYield 82.4%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Heat a suspension of 4-bromo-N-methyl-benzenesulfonamide (0.51 g, 2.0 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (0.81 g, 3.06 mmol), caesiumfluoride (0.93 g, 6.12 mmol) and tetrakis(triphenylphosphino)palladium(0) (230 mg, 0.2 mmol) in 12 mL THF to 60° C. for 4 h. Remove the solvent under vacuum and add ethyl acetate, wash the organic layer with water followed by saturated sodium chloride solution. Filter through a hydrophobic filter paper and remove the solvent under vacuum. Further purify the resulting residue by column chromatography, eluting with a gradient from 100:0 to 35:65 hexanes:ethyl acetate to afford the title compound (0.51 g) as a gray solid. MS (m/e): 310 (M+H).

Workup

  1. temperatureHeat
  2. customRemove the solvent under vacuum
  3. additionadd ethyl acetate
  4. washwash the organic layer with water
  5. filtrationFilter through a hydrophobic filter paper
  6. customremove the solvent under vacuum
  7. customFurther purify the resulting residue by column chromatography
  8. washeluting with a gradient from 100:0 to 35:65 hexanes

Sources & evidence

ORD record
ord-81c1c0c664f340f7a1d2db29ad3c7c95
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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