Tetramethyltin → HCID 136344008, compound

HRID 1847259Notes

Reaction equation

HRID 1847259 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:19])=[C:10]2[C:17]([CH3:18])=[N:16][S:15][C:11]2=[C:12](Br)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:20][Sn](C)(C)C>CN(C=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:5][C:6]([C:8]1[C:9]([OH:19])=[C:10]2[C:17]([CH3:18])=[N:16][S:15][C:11]2=[C:12]([CH3:20])[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 136343979HCID 136343979, compound

Product 1

HCID 136344008HCID 136344008, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 7-bromo-4-hydroxy-3-methyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid butyl ester (0.338 mmol) in DMF (2.05 mL) was added tetramethyltin (0.67 mmol) and PdCl2(PPh3)2 (0.0338 mmol). The reaction mixture was stirred at 120° C. for 1 h. After cooling to r.t., the mixture was partitioned between water (100 mL) and EtOAc (100 mL). The organic layer was washed with brine and water, then dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel. Eluting with 0-20% EtOAc/CH2Cl2, gave the title compound (38.1 mg) as a white solid: MS (m/z) 281.2 (M+1).

Workup

  1. temperatureAfter cooling to r.t.
  2. customthe mixture was partitioned between water (100 mL) and EtOAc (100 mL)
  3. washThe organic layer was washed with brine and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washEluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-f96709d0683442f289cdb67bfd1bf2ca
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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