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

HRID 639026노트

반응식

HRID 639026 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.[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

참가 물질

8

반응물 3

HCID 11661Tetramethyltin2회HCID 433294Lithium ChlorideHCID 21873784Methyl 7-bromo-3,4-dihydro-3-oxo-2H-pyrido[3,2-b]-1,4-thiazine-6-carboxylate

생성물 1

HCID 21873746Methyl 7-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate수율 44.2%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d5c1494e26644e518a25b61c2715b13b
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691850B2

반응 노트

불러오는 중…