Tert-Butanesulfinamide → HCID 86689260, 화합물

HRID 1409520노트

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HRID 1409520 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2=O.[CH3:18][C:19]([S:22]([NH2:24])=[O:23])([CH3:21])[CH3:20]>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2=[N:24][S:22]([C:19]([CH3:21])([CH3:20])[CH3:18])=[O:23]

참가 물질

6

반응물 2

HCID 3382465Tert-ButanesulfinamideHCID 574756367-Bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one

생성물 1

HCID 86689260HCID 86689260, 화합물

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

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온도
75 °C

실험 절차

A mixture of 7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one (20 g, 64.4 mmol), 2-methyl-2-propanesulfinamide (23.42 g, 193 mmol) and titanium (IV) ethoxide (45.3 mL, 219 mmol) in dry THF 250 mL was heated at 75° C. overnight. The mixture was cooled to RT, then brine was added while stirring. The resulting suspension was filtered through celite, and the solid was washed with EtOAc. The filtrate was washed with brine, dried over sodium sulfate and concentrated. The crude material was purified by column chromatography with gradient of 0-30% EtOAc/Hexane to give the desired product as an orange solid. MS m/z=415.0 [M+H]+.

후처리

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe resulting suspension was filtered through celite
  3. washthe solid was washed with EtOAc
  4. washThe filtrate was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography with gradient of 0-30% EtOAc/Hexane

출처 및 근거

ORD 기록
ord-dc647cd6208e461e8933ff46b8d5dc64
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921363B2

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