Dimethylformamide → HCID 86617421, compound

HRID 2076669Notes

Reaction equation

HRID 2076669 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].I[C:8]1[CH:9]=[C:10]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=1.[OH:20][C:21]1[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[C:30]([CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][CH:41]=2)[C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].CN(C)C=O>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[OH:20][C:21]1[C:33]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:31]=[C:30]([CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=3)=[CH:42][CH:41]=2)[C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 67119153Tert-butyl 2-hydroxy-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoateHCID 67119370N-(3-iodophenyl)-N-methylmethanesulfonamide

Product 1

HCID 86617421HCID 86617421, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

After [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (82 mg, 0.1 mmol), 1,1′-bis(diphenylphosphino)ferrocene (166 mg, 0.3 mmol) and cesium carbonate (460 mg, 3 mmol) were added to a solution of N-(3-iodophenyl)-N-methylmethanesulfonamide (310 mg, 1 mmol) and tert-butyl 2-hydroxy-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate (494 mg, 1 mmol) obtained in Example (22-4) in 1,4-dioxane (5 ml) and the mixture was stirred under heating at 60° C. for 4 hours, the mixture was left to stand at room temperature overnight. N,N-dimethylformamide (5 ml) was added to the reaction mixture and the mixture was stirred under heating at 70° C. for 9 hour and left to stand at room temperature for one week. The reaction mixture was poured into water and extracted with ethyl acetate (twice). The organic layer was successively washed with water and a saturated aqueous NaCl solution (twice) and dried with anhydrous magnesium sulfate. After the residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1), recrystallization was carried out using tetrahydrofuran and diisopropyl ether to give the title compound as a grayish white crystal (115 mg, yield: 21%).

Workup

  1. waitthe mixture was left
  2. stirringthe mixture was stirred
  3. temperatureunder heating at 70° C. for 9 hour
  4. waitleft
  5. waitto stand at room temperature for one week
  6. extractionextracted with ethyl acetate (twice)
  7. washThe organic layer was successively washed with water
  8. dry with materiala saturated aqueous NaCl solution (twice) and dried with anhydrous magnesium sulfate
  9. customAfter the residue obtained
  10. customby removing the solvent under reduced pressure
  11. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1), recrystallization

Sources & evidence

ORD record
ord-6442f7f199be4ded80dd2358cb98284d
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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