Tetramethyltin → HCID 45097512, compound

HRID 1192537Notes

Reaction equation

HRID 1192537 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([O:15][CH3:16])=[O:14])[N:3]=1.[CH3:17][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>[OH:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH3:17])=[N:3][C:4]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 18698155Methyl 1-chloro-4-hydroxyisoquinoline-3-carboxylate

Product 1

HCID 45097512HCID 45097512, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 1-chloro-4-hydroxyisoquinoline-3-carboxylate (1.00 g, 4.21 mmol, from Aldrich), tetramethylstannane (3.01 g, 16.8 mmol), and bis(triphenylphosphine)-palladium(II) chloride (0.295 g, 0.421 mmol) in N,N-dimethylformamide (30 mL) was stirred at 130° C. for 30 minutes. The mixture was cooled to room temperature, quenched with water and then filtered. The filtrate was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified on silica gel chromatography, eluting with 0 to 10% MeOH in dichloromethane, to give the desired product (0.80 g, 88%). LCMS calculated for C12H12NO3 (M+H)+: m/z=218.1; Found: 218.1.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with water
  3. filtrationfiltered
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on silica gel chromatography
  9. washeluting with 0 to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-82a0ef3ed051430eaab47f535b8ad606
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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