Methyl 2-bromothiazole-5-carboxylate → Methyl 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylate

HRID 561198ノート

反応式

HRID 561198 の反応式
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[F:11][C:12]([F:27])([F:26])[C:13]1[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=1[O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>O1CCOCC1.O>[F:27][C:12]([F:11])([F:26])[C:13]1[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:2]2[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=2)[CH2:18][CH2:17]1

参加物

5

反応物 2

HCID 2773502Methyl 2-bromothiazole-5-carboxylateHCID 50187904-[2-(Trifluoromethyl)phenoxy]piperidine

生成物 1

HCID 57659049Methyl 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
82.5 °C

実験手順

A mixture of methyl 2-bromo-1,3-thiazole-5-carboxylate (10 g, 45 mmol) and 4-[2-(trifluoromethyl)phenoxy]piperidine (12.1 g, 50 mmol) in dioxane (160 mL) was heated at 80-85° C. overnight. After cooling, the mixture was diluted with water and extracted with EtOAc. The EtOAc extract was washed twice with water, dried (Na2SO4) and concentrated. The crude material was purified by column chromatography on silica gel (eluting with 50% EtOAc/hexanes) to afford the title compound as a pale yellow oil.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed twice with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography on silica gel (eluting with 50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-52950cb1f6af416aaadcf818869a573e
出典データセット
uspto-grants-2011_11
特許番号
US08063224B2

反応ノート

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