Potassium Carbonate → HCID 59855502, compound

HRID 2113207Notes

Reaction equation

HRID 2113207 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4](C)[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1.[CH:17]1[C:25]2[C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[O:22][C:21]=2[C:20]([C:30]2[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=2)=[CH:19][CH:18]=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:16])[CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:33]2[CH:34]=[CH:35][C:30]([C:20]3[C:21]4[O:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[C:25]=4[CH:17]=[CH:18][CH:19]=3)=[CH:31][CH:32]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 59655966(4-(Dibenzo[b,d]furan-4-yl)phenyl)boronic acidHCID 60670774HCID 60670774, compound

Product 1

HCID 59855502HCID 59855502, compoundYield 75.5%

Reagents, catalysts & solvents 4

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

Procedure

A solution of 3-(4-bromophenylmethylsulfanyl)-2-methylpropanoic acid methyl ester (0.260 g, 0.82 mmol), 4-(4-dibenzofuranyl)benzeneboronic acid (0.236 g, 086 mmol) and Pd(PPh3)4 (0.052 g, 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 (280 mg, 67%) as an oil. 1H NMR (CDCl3), 8.01 (d, J=8 Hz, 2H), 7.94 (d, J=8 Hz, 2H), 7.78 (d, J=8 Hz, 2H), 7.66 (m, 4H), 7.42 (m, 5H), 3.79 (s, 2H), 3.71 (s, 3H), 2.73 (s, 2H), 1.27 (s, 6H). LCMS 504 (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-04f7e06226534ab9ad46ea35abc1e2b6
Source dataset
uspto-grants-2009_04
Patent number
US07524878B2

Reaction notes

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