Tetramethyltin → HCID 68427942, compound

HRID 642328Notes

Reaction equation

HRID 642328 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:23])=[O:5])[CH3:2].[CH3:24][Sn](C)(C)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH3:24])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:23])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 86617356HCID 86617356, compound

Product 1

HCID 68427942HCID 68427942, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-bromo-2-(4-fluoro-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (140 mg, 0.35 mmol), tetramethyltin (98 μL, 0.70 mmol) and bis(triphenylphosphine)palladium(II) dichloride (25 mg, 0.03 mmol) in dimethylformamide (2.5 mL) was stirred at 130° C. for 45 min before it was cooled to room temperature, quenched with water, filtered. The filtrate was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a white solid (66 mg): MS: (+) m/z 333.0 (M+1).

Workup

  1. temperaturewas cooled to room temperature
  2. customquenched with water
  3. filtrationfiltered
  4. customThe filtrate was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-d800d205ce70494393be7f3594e82066
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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