Tetramethyltin → Methyl 7-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

HRID 723529Notes

Reaction equation

HRID 723529 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.[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>[CH3:17][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

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 21873784Methyl 7-bromo-3,4-dihydro-3-oxo-2H-pyrido[3,2-b]-1,4-thiazine-6-carboxylate

Product 1

HCID 21873746Methyl 7-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Methyl 7-bromo-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (Example 304b) (1.50 g, 4.95 mmol), tetramethyltin (1.71 mL, 12 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.84 g, 1.2 mmol) in dimethylformamide (30 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 (10-50% ethyl acetate/petroleum ether) gave the title compound (1.0 g, 85%).

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. washwashed through with ethyl acetate
  3. customevaporated

Sources & evidence

ORD record
ord-1fd5469ce63d4393b1504017a77771ba
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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