Ethyl Acetate → HCID 22390221, compound

HRID 1072339Notes

Reaction equation

HRID 1072339 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:17])[C:9]2[N:10]=[CH:11][N:12]3[CH:16]=[CH:15][S:14][C:13]=23)[CH:5]=[N:6][CH:7]=1.C(B(CC)[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)C.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.[O-2].[O-2].[Mn+4].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>[N:6]1[CH:5]=[C:4]([C:8]([C:9]2[N:10]=[CH:11][N:12]3[CH:16]=[CH:15][S:14][C:13]=23)=[O:17])[CH:3]=[C:2]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 22390351HCID 22390351, compound

Product 1

HCID 22390221HCID 22390221, compoundYield 34.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A ketone compound (1.96 g) was prepared in substantially the same manner as in step b) of Synthesis Example 1, except that 2.77 g of 7-[(5-bromopyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole and 2.00 g of manganese dioxide were used as the starting compounds. The ketone compound (616 mg) was dissolved in 20 ml of N,N-dimethylformamide to prepare a solution. Diethyl(3-pyridyl)borane (588 mg), 232 mg of tetrakis(triphenylphosphine)palladium(0), and 552 mg of potassium carbonate were added to the solution at room temperature under an argon atmosphere. The mixture was stirred at 90° C. for 2.5 hr. Ethyl acetate (200 ml) was added to the reaction solution, and the organic layer was washed four times with 80 ml of water and once with saturated brine. The washed organic layer was dried over anhydrous magnesium sulfate and was filtered. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel (chloroform/methanol=20/1 →10/1) to give 428 mg of 7-([3,3′]bipyridinyl-5-yl)carbonylimidazo[5,1-b]thiazole.

Workup

  1. customof Synthesis Example 1
  2. customto prepare a solution
  3. washthe organic layer was washed four times with 80 ml of water
  4. dry with materialThe washed organic layer was dried over anhydrous magnesium sulfate
  5. filtrationwas filtered
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by chromatography on silica gel (chloroform/methanol=20/1 →10/1)

Sources & evidence

ORD record
ord-d05e59bd4107469b8ed571ef6d8e3a20
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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