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

HRID 874343
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HRID 874343 반응식
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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

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온도
-35 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-85ba2d5711314990b7805c09417a63a5
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08980888B2

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