Methyl iodide → HCID 58827051, 화합물

HRID 1877968노트

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HRID 1877968 반응식
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]([C:10]3[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][C:13]([C:22]#[N:23])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH2:6][C:5]=12.[Li+].[CH3:25][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[CH3:25][C:9]1([C:10]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([C:22]#[N:23])=[CH:12][CH:11]=2)[N:4]2[CH:3]=[N:2][CH:1]=[C:5]2[CH2:6][CH2:7][CH2:8]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 588270486-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)biphenyl-3-carbonitrile

생성물 1

HCID 58827051HCID 58827051, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

To a solution of 6-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)biphenyl-3-carbonitrile (53 mg, 0.177 mmol) in THF (2 mL) at −40° C. is added LHMDS (1.0 M in THF, 0.27 mL, 0.27 mmol). The resulting brown solution is stirred at −30° C. for 0.5 h. To the reaction mixture is added methyl iodide (0.017 mL, 0.272 mmol) and the mixture is warmed up to ambient temperature and stirred overnight. The reaction mixture is quenched by saturated aqueous NH4Cl and the reaction is partitioned between CH2Cl2 and brine. The organic layer is washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude oil, which is subject to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 314 (M+H).

후처리

  1. temperaturethe mixture is warmed up to ambient temperature
  2. stirringstirred overnight
  3. customThe reaction mixture is quenched by saturated aqueous NH4Cl
  4. customthe reaction is partitioned between CH2Cl2 and brine
  5. washThe organic layer is washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto give the crude oil, which
  9. washeluting with MeOH

출처 및 근거

ORD 기록
ord-e02fdf0fc9944a1789dcf384974a97df
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314097B2

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