Cesium carbonate → HCID 67232912, compound

HRID 2368710Notes

Reaction equation

HRID 2368710 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:10](=[O:11])[CH:9]2[CH:12]=[C:13](Br)[S:14][CH:8]2[C:7]1=[O:16])[CH3:2].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.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>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:10](=[O:11])[CH:9]2[CH:12]=[C:13]([C:23]3[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[S:14][CH:8]2[C:7]1=[O:16])[CH3:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 67232936HCID 67232936, compound

Product 1

HCID 67232912HCID 67232912, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, (2-bromo-4,6-dioxo-3a,4,6,6a-tetrahydro-thieno[2,3-c]pyrrol-5-yl)-acetic acid ethyl ester, example 1-d (431 mg, 1.35 mmol), 4-methoxy-phenyl boronic acid (309 mg, 2.0 mmol), cesium carbonate (1.10 g, 3.4 mmol), and tetrakis(triphenylphosphine)palladium(0) (157 mg, 0.14 mmol) were suspended in 8 mL of ethylene glycol dimethyl ether. The reaction mixture was heated at reflux temperature for 5 hours, cooled to room temperature, and diluted with ethyl acetate. The organic mixture was successively washed with saturated sodium bicarbonate and brine solutions. The organic fractions were dried over anhydrous sodium sulfate and concentrated to a crude solid residue, which was then purified by column chromatography, eluting the title compound from silica gel with a gradient of (5-30%) ethyl acetate in hexanes to yield 197 mg of a white solid. MS: (+) m/z 348.05 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 5 hours
  3. washThe organic mixture was successively washed with saturated sodium bicarbonate and brine solutions
  4. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  5. concentrationconcentrated to a crude solid residue, which
  6. customwas then purified by column chromatography
  7. washeluting the title compound from silica gel with a gradient of (5-30%) ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b50b25152edf40ca955e63a4abfc87e8
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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