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Potassium Carbonate → (8R)-8-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

HRID 1424112
ノート
印刷プレビュー

反応式

HRID 1424112 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[N:15]4[CH2:16][CH2:17][S:18][C@:19]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])([CH3:21])[CH2:20][C:14]4=[N:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:31]([N:33]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[N:34]1)[CH3:32].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C>[Si:24]([O:23][CH2:22][C@:19]1([CH3:21])[S:18][CH2:17][CH2:16][N:15]2[C:11]([C:8]3([C:5]4[CH:6]=[CH:7][C:2]([C:36]5[CH:35]=[N:34][N:33]([CH2:31][CH3:32])[CH:37]=5)=[CH:3][CH:4]=4)[CH2:10][CH2:9]3)=[N:12][N:13]=[C:14]2[CH2:20]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 86712920(8R)-3-[1-(4-Bromophenyl)cyclopropyl]-8-({[t-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

生成物 1

HCID 89977493(8R)-8-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine
収率 89.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

The compound (600 mg, 1.18 mmol) obtained in Example 52-1), 1-ethyl-1H-pyrazole-4-boronic acid pinacol ester (314 mg, 1.42 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (93 mg, 0.12 mmol), and potassium carbonate (489 mg, 3.54 mmol) were dissolved in a mixed solvent of 1,4-dioxane (4 mL) and water (2 mL), and the mixture was stirred at 90° C. for 5 h. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60 to 100:0) to obtain the title compound (551 mg, 89%) as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60 to 100:0)

出典と根拠

ORDレコード
ord-5a4536a7c3844de4bd9bc4871c30bb99
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927536B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート