Pyridine → (9S)-9-{4-[2-chloro-5-(trifluoromethyl)phenoxy]phenyl}-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405820ノート

反応式

HRID 1405820 の反応式
N1C=CC=CC=1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1B(O)O.[O:21]=[S:22]1(=[O:39])[CH2:27][CH2:26][N:25]2[CH2:28][CH2:29][CH2:30][C@@H:31]([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)[C:24]2=[N:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N.C(O[Cu]OC(=O)C)(=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[O:38][C:35]1[CH:34]=[CH:33][C:32]([C@H:31]2[C:24]3=[N:23][S:22](=[O:39])(=[O:21])[CH2:27][CH2:26][N:25]3[CH2:28][CH2:29][CH2:30]2)=[CH:37][CH:36]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 10796Cesium carbonateHCID 27826702-Chloro-5-(trifluoromethyl)phenylboronic acidHCID 667484964-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol

生成物 1

HCID 66748026(9S)-9-{4-[2-chloro-5-(trifluoromethyl)phenoxy]phenyl}-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide収率 0.6%

試薬・触媒・溶媒 2

HCID 178476681HCID 178476681、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

Diacetoxycopper (907 mg) was added to a mixture of pyridine (0.606 mL), 2-chloro-5-(trifluoromethyl)phenylboronic acid (459 mg), 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (700 mg) and cesium carbonate (814 mg) in MeCN (25 mL). The mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube for 2 days. The insoluble material was removed by filtration, and the filtrate was diluted with water, and extracted with EtOAc. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. Silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo to give the title compound (5.9 mg) as pale yellow gum.

後処理

  1. customThe insoluble material was removed by filtration
  2. additionthe filtrate was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additionSilica-gel was added
  7. customthe volatiles were removed in vacuo
  8. customwas purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eb249035b06d4a3389a4cc0fe3270292
出典データセット
uspto-grants-2014_12
特許番号
US08916551B2

反応ノート

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