Dimethyl Sulfoxide → HCID 131727230, compound

HRID 2375965Notes

Reaction equation

HRID 2375965 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.[C:36]([O:40][C:41](=[O:65])[CH2:42][N:43]([S:55]([C:58]1[CH:63]=[CH:62][C:61](Br)=[CH:60][CH:59]=1)(=[O:57])=[O:56])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=1)([CH3:39])([CH3:38])[CH3:37].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C>[C:36]([O:40][C:41](=[O:65])[CH2:42][N:43]([S:55]([C:58]1[CH:63]=[CH:62][C:61]([C:16]2[CH:15]=[CH:14][C:13]([C:12]3[C:11]4[CH:28]=[CH:29][CH:30]=[CH:31][C:10]=4[O:9][C:8]=3[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:18][CH:17]=2)=[CH:60][CH:59]=1)(=[O:57])=[O:56])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 62657Potassium Phosphate, TribasicHCID 11750201HCID 11750201, compoundHCID 69550132HCID 69550132, compound

Product 1

HCID 131727230HCID 131727230, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 (268 mg 0.653 mmol) in anhyd DMSO (5 mL) was added to a stirred suspension of tert-Butyl-[(4-bromobenzenesulfonyl)-(3-trifluoromethylbenzyl)amino]-acetate (296 mg, 0.58 mmol) and tripotassium phosphate (0.37 g, 1.76 mmol) in anhyd DMSO (5 mL). [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-DCM complex (60 mg, 0.07 mmol) was added as a solid, and the resulting suspension was heated to 80° C. for 25 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered though celite, and washed with sat'd aq LiCl (3×10 mL), sat'd aq NaCl (1×10 mL), dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (heptane) afforded the title compound as a white solid (95 mg).

Workup

  1. addition[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-DCM complex (60 mg, 0.07 mmol) was added as a solid
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered though celite
  4. washwashed with sat'd aq LiCl (3×10 mL)
  5. dry with materialdried over anhyd MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash column chromatography (heptane)

Sources & evidence

ORD record
ord-df9c026b8e35466e85c0d85224929958
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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