Potassium Carbonate → HCID 69002537, compound

HRID 1909796Notes

Reaction equation

HRID 1909796 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[S:20]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21]1.C([O-])([O-])=O.[K+].[K+]>CCO.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:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:22]3[CH:23]=[CH:24][S:20][CH:21]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 59752892HCID 59752892, compound

Product 1

HCID 69002537HCID 69002537, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of step 2 (0.5 g, 1.4 mmol), 3-thiophenboronic acid (0.2 g, 1.4 mmol), K2CO3 (1.1 g, 8.1 mmol) and (Ph3P)4Pd (0.08 g, 0.07 mmol) in EtOH (10 mL) was heated to reflux for 24 h. After the solids were filtered off, the filtrate was concentrated to dryness. The residue was purified by a column chromatography on silica gel to yield the title compound (0.4 g, 91%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. filtrationAfter the solids were filtered off
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-4fc764aabfd34988a5e2119dd266f021
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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