Ammonium Chloride → HCID 23114695, 화합물

HRID 2080362노트

반응식

HRID 2080362 반응식
C([Mg]Cl)(C)C.[CH2:6]([O:9][C:10]1[C:11](Br)=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:7]=[CH2:8].[F:17][C:18]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:19]=1[CH:20]=[O:21].[Cl-].[NH4+]>O1CCCC1>[CH2:6]([O:9][C:10]1[C:11]([CH:20]([C:19]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:18]=2[F:17])[OH:21])=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:7]=[CH2:8]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 23028574Pyridine, 2-bromo-3-(2-propenyloxy)-HCID 178418918HCID 178418918, 화합물

생성물 1

HCID 23114695HCID 23114695, 화합물수율 45.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Under an argon atmosphere, a tetrahydrofuran solution (1.5 ml, 3 mmol) of isopropylmagnesium chloride was added dropwise to a tetrahydrofuran (2 ml) solution of the 3-allyloxy-2-bromopyridine (642 mg, 3 mmol) obtained in Referential Example 8 under ice cooling. The resulting mixture was stirred at room temperature for 60 minutes. To the resulting brown solution was added dropwise 2,5-difluorobenzaldehyde (328 μl, 3 mmol) under ice cooling. The temperature of the reaction mixture was gradually raised to room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The solvent was then dried and the residue obtained by concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the title compound (375 mg, 45%) as an oil.

후처리

  1. customobtained in Referential Example 8 under ice cooling
  2. temperatureThe temperature of the reaction mixture was gradually raised to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. customThe solvent was then dried
  5. customthe residue obtained by concentration under reduced pressure
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-9a0ef0f3aae44f69a0a47b02959681d6
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932271B2

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