Potassium Phosphate, Tribasic → HCID 60147144, compound

HRID 2375971Notes

Reaction equation

HRID 2375971 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.Br[C:33]1[CH:38]=[CH:37][C:36]([C:39](=[O:51])[CH2:40][CH:41]2[C:46](=[O:47])[O:45][C:44]([CH3:49])([CH3:48])[O:43][C:42]2=[O:50])=[CH:35][CH:34]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.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:33]2[CH:38]=[CH:37][C:36]([C:39](=[O:51])[CH2:40][CH:41]3[C:46](=[O:47])[O:45][C:44]([CH3:49])([CH3:48])[O:43][C:42]3=[O:50])=[CH:35][CH:34]=2)=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 11617066HCID 11617066, compoundHCID 11750201HCID 11750201, compound

Product 1

HCID 60147144HCID 60147144, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×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 anhydrous 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 anhydrous 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 hrs. The reaction mixture was cooled to room temperature, diluted with diethyl ether (150 mL), washed with water (2×50 mL), brine (3×50 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 50-60% ethyl acetate/heptane as eluent, afforded the title compound as an off-white solid (502 mg): 1H-NMR (DMSO-d6, 300 MHz): δ 8.12 (2H, d, J=8 Hz, Ar—H), 7.92 (4H, d, J=6 Hz, Ar—H), 7.53-7.69 (4H, m, Ar—H), 7.26 (7H, m, Ar—H), 4.82 (1H, s, CH), 4.26 (2H, s, PhCH2), 3.86 (2H, CH2CO), 1.84 (3H, s, Me), 1.74 (3H, s, Me).

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), brine (3×50 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-1f7b70f4c7624572935a6cf656aaf965
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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