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Cesium carbonate → 3-(1-Benzothien-5-yloxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide

HRID 548658
ノート
印刷プレビュー

反応式

HRID 548658 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:37])[CH2:25][O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12].Br[C:39]1[CH:40]=[CH:41][C:42]2[S:46][CH:45]=[CH:44][C:43]=2[CH:47]=1>CC(N(C)C)=O>[S:46]1[C:42]2[CH:41]=[CH:40][C:39]([O:7][C:8]3[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:37])[CH2:25][O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:28]([CH3:29])[CH3:30])[CH:31]([CH3:33])[CH3:32])[CH:22]=3)[C:11]([NH:13][C:14]3[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=3)=[O:12])=[CH:47][C:43]=2[CH:44]=[CH:45]1
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

5

反応物 3

HCID 10796Cesium carbonateHCID 27765785-Bromo-1-benzothiopheneHCID 536296193-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[((1S)-1-methyl-2-{[tris(1-methylethyl)silyl]oxy}ethyl)oxy]benzamide

生成物 1

HCID 576631673-(1-Benzothien-5-yloxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide収率 34.5%

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
200 °C

実験手順

Cesium carbonate (163 mg, 0.05 mmol) was added to a solution of 3-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide (225 mg, 0.5 mmol), bromotris(triphenylphosphine)copper1 (93 mg, 0.1 mmol) and 5-bromobenzothiophene (107 mg, 0.5 mmol) in dimethylacetamide (2.5 mL) and the stirred mixture heated at 200° C. in a “Biotage Initiator” microwave for 4 hours. The mixture was cooled to ambient temperature and pressure, poured onto water (40 mL) and extracted with ethyl acetate (3×15 mL), the combined organic layers washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 40% ethyl acetate in isohexane, to give the desired compound (100 mg).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. additionpressure, poured onto water (40 mL)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. washthe combined organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas chromatographed on silica
  8. washeluting with 40% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-cc02142da8e24b1bb23cc6fda2e316ce
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07943607B2

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