Sodium Carbonate → HCID 178420875, compound

HRID 411628Notes

Reaction equation

HRID 411628 reaction equation
I[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[S:7]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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>[S:7]1[CH:11]=[CH:10][C:9]([C:2]2[N:3]=[CH:4][NH:5][CH:6]=2)=[CH:8]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 178506559HCID 178506559, compound

Product 1

HCID 178420875HCID 178420875, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-iodo-1H-imidazole (0.24 g, 1.25 mmol) and Pd(PPh3)4 (72 mg, 0.06 mmol) in DME (12.5 mL) was degased by purging with argon for 10 min. Thiophene-3-boronic acid (0.32 g, 2.50 mmol) and Na2CO3 (2.5 mL of a 2M solution in water) were added. The mixture was heated to reflux for 18 h. After cooling to RT, the solvent was removed under reduced pressure. The residue was subjected to flash chromatography (4% MeOH/CH2Cl2, silica gel) to give 0.16 g of the desired product as an off-white solid. MS(ES+) m/z 151.3 (M+H+).

Workup

  1. customby purging with argon for 10 min
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 18 h
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9030fee389954f8b950924326245d822
Source dataset
uspto-grants-2003_05
Patent number
US06559172B1

Reaction notes

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