Dimethyl Sulfoxide → HCID 60147144, compound

HRID 900485Notes

Reaction equation

HRID 900485 reaction equation
[CH2:1]([C:8]1[O:9][C:10]2[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=2[C:12]=1[C:13]1[CH:18]=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.Br[C:37]1[CH:42]=[CH:41][C:40]([C:43](=[O:55])[CH2:44][CH:45]2[C:50](=[O:51])[O:49][C:48]([CH3:53])([CH3:52])[O:47][C:46]2=[O:54])=[CH:39][CH:38]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)C>[CH2:1]([C:8]1[O:9][C:10]2[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=2[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([C:37]2[CH:42]=[CH:41][C:40]([C:43](=[O:55])[CH2:44][CH:45]3[C:50](=[O:51])[O:49][C:48]([CH3:53])([CH3:52])[O:47][C:46]3=[O:54])=[CH:39][CH:38]=2)=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 62657Potassium Phosphate, TribasicHCID 11617066HCID 11617066, compoundHCID 11750201HCID 11750201, compound

Product 1

HCID 60147144HCID 60147144, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-benzyl-3-[4′-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-benzofuran (500 mg, 1.22 mmol) in anhyd DMSO (5 mL) was added to a stirred suspension of 5-[2-(4-bromophenyl)-2-oxoethyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione (436 mg, 1.22 mmol) and tripotassium phosphate (1.04 g, 4.88 mmol) in anhyd DMSO (5 mL). [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-DCM complex (100 mg, 0.12 mmol) was added as a solid, and the resulting suspension was heated to 80° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with diethyl ether (150 mL), washed with water (2×50 mL), sat'd aq NaCl (3×50 mL), dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (50-60% ethyl acetate in heptane) afforded the title compound as an off-white solid (502 mg).

Workup

  1. addition[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-DCM complex (100 mg, 0.12 mmol) was added as a solid
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with water (2×50 mL)
  4. dry with materialdried over anhyd MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (50-60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-50c5c027d2d044e9988d527fae3942c1
Source dataset
uspto-grants-2008_04
Patent number
US07358364B2

Reaction notes

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