Potassium Carbonate → HCID 59855502, compound

HRID 2375974Notes

Reaction equation

HRID 2375974 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1.[CH:16]1[C:24]2[C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[O:21][C:20]=2[C:19]([C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:32]2[CH:33]=[CH:34][C:29]([C:19]3[C:20]4[O:21][C:22]5[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=5[C:24]=4[CH:16]=[CH:17][CH:18]=3)=[CH:30][CH:31]=2)=[CH:10][CH:9]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 59655966(4-(Dibenzo[b,d]furan-4-yl)phenyl)boronic acidHCID 59855504HCID 59855504, compound

Product 1

HCID 59855502HCID 59855502, compoundYield 72.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-bromophenylmethylsulfanyl)-propanoic acid methyl ester (289 mg, 1 mmol), 4-(4-dibenzofuranyl)benzeneboronic acid (302 mg, 1.05 mmol) and Pd(PPh3)4 (52 mg, 5 mol %) in toluene (10 mL) and ethanol (3.0 mL) was treated with 2 M K2CO3 (1.5 mL). The reaction mixture was heated to reflux for 2 h, cooled to room temperature, diluted with ethyl acetate (100 mL). The organic layer was washed successively with 2% aq HCl and sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (2-10% ethyl acetate in heptane) gave 3-(4′-dibenzofuran-4-yl-biphen-4-ylmethylsulfanyl)-propanoic acid methyl ester (330 mg, 72%) as white solid. 1H NMR (CDCl3), 8.01 (d, J=8 Hz, 2 H), 7.94 (d, J=8 Hz, 2 H), 7.78 (d, J=8 Hz, 2 H), 7.66 (m, 4 H), 7.42 (m, 5 H), 3.81 (s, 2 H), 3.71 (s, 3 H), 2.76 (t, J=6 Hz, 2 H), 2.56 (t, J=6 Hz, 2 H). LCMS 475 (M++23).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. washThe organic layer was washed successively with 2% aq HCl and sat. aq NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (2-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-973026ed61a547c7b1aa02eeb6f5f452
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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