2-(Tributylstannyl)-1,3-thiazole → HCID 136389262, compound

HRID 642347Notes

Reaction equation

HRID 642347 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][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:28]1[S:29][CH:30]=[CH:31][N:32]=1)CCC>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]([C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 866173544-Bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 136389262HCID 136389262, compoundYield 11.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (246 mg, 0.65 mmole), 2-(tributylstannyl)thiazole (410 μl, 1.30 mmole) and bis(triphenylphosphine)-palladium(II) dichloride (46 mg, 0.06 mmole) in dimethylformamide (3 ml) was stirred at 130° C. for one hour 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. Fractions containing the title compound was concentrated and repurified by preparative TLC with a gradient of methanol, dichloromethane and acetic acid to give the title compound as a yellow solid (29 mg). MS: (+) m/z 383.87 (M+1), m/z 406.00 (M+Na+).

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
  9. additionFractions containing the title compound
  10. concentrationwas concentrated
  11. customrepurified by preparative TLC with a gradient of methanol, dichloromethane and acetic acid

Sources & evidence

ORD record
ord-17bd025d5c804e3ea65a8566396c697e
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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