Tetramethyltin → HCID 68428023, compound

HRID 642562Notes

Reaction equation

HRID 642562 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]([CH3:19])([CH3:18])[CH3:17])[S:15][C:8]=2[C:7]=1[OH:20])=[O:5])[CH3:2].[CH3:21][Sn](C)(C)C>CN(C=O)C.C(OCC)(=O)C.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]([CH3:21])[C:9]2[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[S:15][C:8]=2[C:7]=1[OH:20])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 11661TetramethyltinHCID 86617377HCID 86617377, compound

Product 1

HCID 68428023HCID 68428023, compoundYield 89.2%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromo-2-tert-butyl-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (145 mg, 0.40 mmol), tetramethyl tin (220 μL, 1.6 mmol), dichlorobis(triphenylphosphine)-palladium II (30 mg, 0.04 mmol) in 2.5 mL anhydrous DMF was heated to 130° C. for 1 h. The reaction mixture was cooled, diluted with ethyl acetate, and washed successively with water, saturated sodium bicarbonate, and brine. The organic fraction was dried over anhydrous sodium sulfate, concentrated to a crude residue and purified by column chromatography (eluting from silica gel with a gradient of 10-50% ethyl acetate in hexanes) to give 105 mg of a white solid. MS (ESI−): m/z 293.4 (M−1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed successively with water, saturated sodium bicarbonate, and brine
  3. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to a crude residue
  5. custompurified by column chromatography (
  6. washeluting from silica gel with a gradient of 10-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7838ab5b4d924290b6dbeac4e64f5bfb
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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