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

HRID 639026Notes

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.[Li+].[Cl-].[Sn](C)(C)(C)[CH3:20]>CN(C=O)C.C(Cl)Cl.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>[CH3:20][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

Conditions

Temperature: 100 °C

Procedure

Methyl 7-bromo-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (1.44 g, 4.75 mmol) was dissolved in DMF (20 mL) and treated with PdCl2(PPh3)2 (167 mg, 0.238 mmol), LiCl (604 mg, 14.2 mmol) and Me4Sn (0.66 mL, 4.75 mmol). The reaction was heated at 100° C. for 30 min, at which point the reaction was no longer proceeding. An additional 0.25 mL of Me4Sn was added and the reaction was heated for an additional 4 h. After cooling, the reaction was diluted with DCM and water. The product was extracted into DCM and the combined extract was dried (Na2SO4) and filtered and the concentrated in vacuo. Purification provided product (500 mg).

Workup

temperaturethe reaction was heated for an additional 4 h
temperatureAfter cooling
extractionThe product was extracted into DCM
extractionthe combined extract
dry with materialwas dried (Na2SO4)
filtrationfiltered
concentrationthe concentrated in vacuo
customPurification

Sources & evidence

ORD record: ord-d5c1494e26644e518a25b61c2715b13b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691850B2

Reaction notes

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