Tetraethyltin → HCID 21873607, compound

HRID 723530Notes

Reaction equation

HRID 723530 reaction equation
Br[C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10][C:9]2[NH:8][C:7](=[O:16])[CH2:6][S:5][C:4]=2[CH:3]=1.[CH2:17]([Sn](CC)(CC)CC)[CH3:18]>CN(C)C=O.CO.C(OCC)(=O)C.[Pd].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>[CH2:17]([C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10][C:9]2[NH:8][C:7](=[O:16])[CH2:6][S:5][C:4]=2[CH:3]=1)[CH3:18]

Participants

7

Reactant 2

HCID 11704TetraethyltinHCID 21873784Methyl 7-bromo-3,4-dihydro-3-oxo-2H-pyrido[3,2-b]-1,4-thiazine-6-carboxylate

Product 1

HCID 21873607HCID 21873607, compoundYield 16.8%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

Methyl 7-bromo-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (Example 304b) (2.00 g, 6.6 mmol), tetraethyltin (3.17 mL, 16 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.6 mmol) in dimethylformamide (40 mL) were heated at 120° C. for 24 h. The mixture was filtered through Kieselguhr, washed through with ethyl acetate and evaporated. Chromatography on silica gel (20-50% ethyl acetate/petroleum ether) gave a mixture of the 7-ethyl and 7-vinyl compounds (0.29 g). This mixture was hydrogenated in methanol/ethyl acetate (2:1, 60 mL) over 10% palladium on carbon (60 mg) (1 atmosphere, room temperature) for 24 h. Filtration and evaporation of solvent gave the product (0.28 g).

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. washwashed through with ethyl acetate
  3. customevaporated
  4. customChromatography on silica gel (20-50% ethyl acetate/petroleum ether) gave
  5. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-213be68eff2d4c3d9c43a25944fff84c
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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