Tert-Butanesulfinamide → N-(6-Bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-ylidene)-2-methylpropane-2-sulfinamide

HRID 1965125노트

반응식

HRID 1965125 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([CH:12]1[CH2:17][CH2:16][CH2:15][O:14][CH2:13]1)[CH2:6][C:5]2=O.[CH3:19][C:20]([S:23]([NH2:25])=[O:24])([CH3:22])[CH3:21]>CC1CCCO1.CCOC(C)=O.O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([CH:12]1[CH2:17][CH2:16][CH2:15][O:14][CH2:13]1)[CH2:6][C:5]2=[N:25][S:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24]

참가 물질

7

반응물 2

HCID 3382465Tert-ButanesulfinamideHCID 584241476-bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-one2회

생성물 1

HCID 67979529N-(6-Bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-ylidene)-2-methylpropane-2-sulfinamide수율 90.1%

시약·촉매·용매 4

HCID 76524Titanium tetraethoxide촉매HCID 962Water용매HCID 73012-Methyltetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

6-Bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-one (Intermediate 27, 1.5 g, 4.82 mmol) and 2-methylpropane-2-sulfinamide (1.052 g, 8.68 mmol) were dissolved in dry 2-methyl-tetrahydrofuran (12 mL). Neat titanium ethoxide (1.788 mL, 8.68 mmol) was added. The resulting mixture was heated by MW at 130° C. for 60 min. The mixture was diluted with EtOAc (150 mL) and water (40 mL) was added dropwise during vigorous stirring of the reaction mixture. The stirring was continued for 15 min. The solid was decanted and the mixture filtered through a pad of diatomaceous earth. The organic layer was separated, dried over MgSO4 and vacuum filtered directly through a pad of silica (approx. 10 g) and concentrated in vacuo to give the title compound (1.8 g, 90% yield). MS (ES+) m/z 414 [M+H]+.

후처리

  1. additionwas added dropwise
  2. customThe solid was decanted
  3. filtrationthe mixture filtered through a pad of diatomaceous earth
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4 and vacuum
  6. filtrationfiltered directly through a pad of silica (approx. 10 g)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1e225fa75cbb45c5aa958e71fc50abf6
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415483B2

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