Tert-Butanesulfinamide → HCID 86689260、化合物

HRID 1409520ノート

反応式

HRID 1409520 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

HCID 86689260HCID 86689260、化合物

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
75 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-dc647cd6208e461e8933ff46b8d5dc64
出典データセット
uspto-grants-2014_12
特許番号
US08921363B2

反応ノート

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