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tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 5-(1,3-thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 490220
ノート
印刷プレビュー

反応式

HRID 490220 の反応式
[Br-].[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Zn+].FC(F)(F)S(O[C:14]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][CH2:16][CH:15]=1)(=O)=O>O1CCCC1>[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:16]1[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:14][CH:15]=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

4

反応物 2

HCID 53978067tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateHCID 178419763HCID 178419763、化合物

生成物 1

HCID 57440157tert-butyl 5-(1,3-thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To the mixture of 2-thiazolylzinc bromide (20 mL, 10 mmol) in dry tetrahydrofuran (30 mL) at 0° C. was added the product from Example 328B (3.3 gm, 10 mmol) and tetrakis(tripehynlphosphine) palladium (0) (10% mole 1.1 g). The mixture was heated at 50° C. for 1 hour, cooled to room temperature, quenched with brine and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 25% ethyl acetate:hexanes) to obtain desired product 1.4 g (60%) as colorless oil. MS (DCI/NH3) m/e 265 (M+H)+.

後処理

  1. temperaturecooled to room temperature
  2. customquenched with brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica gel, 25% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-e24430c2f5b0478ebe16d2baf030804a
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07528134B2

反応ノート

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