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Water → Methyl 2-bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylate

HRID 874343
ノート
印刷プレビュー

反応式

HRID 874343 の反応式
O1CCCC1.[Br:6][C:7]1[N:8]=[C:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]2[C:19]=1Br.C([Mg]Br)(C)C.O>C(OCC)(=O)C>[Br:6][C:7]1[N:8]=[C:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]2[CH:19]=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

6

反応物 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 90383288Methyl 2,3-dibromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylateHCID 178418365HCID 178418365、化合物

生成物 1

HCID 90383213Methyl 2-bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylate収率 68.2%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
-35 °C

実験手順

A tetrahydrofuran (150 ml) solution of the methyl 2,3-dibromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylate (13 g) obtained in (Example 2.7) <Step 1> was cooled to −35° C. Thereafter, isopropylmagnesium bromide (95 ml, 1 M tetrahydrofuran solution) was added to the solution over 20 minutes, while keeping the temperature at −30° C. or less, and the reaction solution was then stirred at −35° C. for 30 minutes. Thereafter, water (350 ml) and ethyl acetate (250 ml) were added to the reaction solution, and insoluble matters were then removed by filtration with Celite. Subsequently, the filtrate was separated into an organic layer and a water layer. The water layer was extracted with ethyl acetate (250 ml), and the organic layers were then gathered. The gathered organic layer was washed with a saturated saline, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=70:30-30:70), so as to obtain the title compound (6.8 g) in the form of a white solid.

後処理

  1. customat −30° C. or less
  2. customwere then removed by filtration with Celite
  3. customSubsequently, the filtrate was separated into an organic layer
  4. extractionThe water layer was extracted with ethyl acetate (250 ml)
  5. washThe gathered organic layer was washed with a saturated saline
  6. distillationthe solvent was then distilled away under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=70:30-30:70)

出典と根拠

ORDレコード
ord-85ba2d5711314990b7805c09417a63a5
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08980888B2

反応ノート

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