Potassium Carbonate → HCID 59655964, compound

HRID 2054581Notes

Reaction equation

HRID 2054581 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)[CH2:9][C:8]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[N:7]1)[CH3:2].[CH:27]1[C:35]2[C:34]3[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=3[O:32][C:31]=2[C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:39]3[C:33]4[O:32][C:31]5[CH:30]=[CH:29][CH:28]=[CH:27][C:35]=5[C:34]=4[CH:36]=[CH:37][CH:38]=3)=[CH:13][CH:12]=2)[CH2:9][C:8]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[N:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 59655957HCID 59655957, compound

Product 1

HCID 59655964HCID 59655964, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of [5-(4-bromo-phenyl)-3-(4-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-acetic acid ethyl ester (0.417 g, 1.0 mmol) and 4-dibenzofuranboronic acid (0.233 g, 1.1 mmol) in toluene (15 mL, X M) was treated with 2 N aq K2CO3 (1.5 mL, xx mmol) and Pd[PPh3]4 (0.058 g, 0.05 mmol). The resulting solution was heated to reflux for 2 h, cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (10% ethyl acetate in heptane) provided [5-(4-Dibenzofuran-4-yl-phenyl)-3-(4-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-acetic acid ethyl ester (0.394 g, 78%) as a white crystalline solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 2 h
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a06875ef6e8943e69560ecd8cdbfb16f
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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