Tetraethyltin → HCID 21873607, 화합물

HRID 723530노트

반응식

HRID 723530 반응식
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]

참가 물질

7

반응물 2

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

생성물 1

HCID 21873607HCID 21873607, 화합물수율 16.8%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 21584119Ethylacetate methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-213be68eff2d4c3d9c43a25944fff84c
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141564B2

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