Hydrochloric Acid → HCID 67314628, 화합물

HRID 1011345노트

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HRID 1011345 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:22]([N:24]([CH2:40][CH3:41])[CH2:25][CH2:26][N:27]([CH2:29][C:30]1[N:35]=[C:34]2[CH2:36][O:37][C:38](=O)[C:33]2=[CH:32][CH:31]=1)[CH3:28])[CH3:23].Cl>C1COCC1>[CH2:40]([N:24]([CH2:22][CH3:23])[CH2:25][CH2:26][N:27]([CH2:29][C:30]1[N:35]=[C:34]2[CH2:36][O:37][C:38](=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:7][C:6]3=[O:11])[C:33]2=[CH:32][CH:31]=1)[CH3:28])[CH3:41]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 59665587HCID 59665587, 화합물

생성물 1

HCID 67314628HCID 67314628, 화합물수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 5-fluoro-1,3-dihydro-indol-2-one (125 mg, 0.83 mmol.) in THF (4 mL) is treated with a solution of lithium bis(trimethylsilyl)amide (1.66 mL of a 1M solution in THF, 1.66 mmol) dropwise. The resulting solution is stirred for 20 min at room temperature. A solution of 2-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-7H-furo[3,4-b]pyridin-5-one (115 mg, 0.41 mmol) in THF (1.5 mL) is added dropwise to the reaction mixture. The resulting solution is stirred at room temperature for 4 h and then poured into 10% aqueous HCl solution (30 mL) previously cooled to 0° C. The ice bath is removed and the solution is stirred at room temperature for 16 h. The yellow solution is then cooled and solid NaHCO3 is carefully added to adjust the solution to pH=8. The aqueous layer is extracted with EtOAc. The combined organic extracts are dried with anhydrous Na2SO4 and concentrated. The solid residue is broken up in isopropyl alcohol to give a yellow solid. The yellow solid is collected by filtration to give the title compound (102 mg, 61%).

후처리

  1. stirringThe resulting solution is stirred at room temperature for 4 h
  2. temperaturepreviously cooled to 0° C
  3. customThe ice bath is removed
  4. stirringthe solution is stirred at room temperature for 16 h
  5. temperatureThe yellow solution is then cooled
  6. additionsolid NaHCO3 is carefully added
  7. extractionThe aqueous layer is extracted with EtOAc
  8. dry with materialThe combined organic extracts are dried with anhydrous Na2SO4
  9. concentrationconcentrated
  10. customto give a yellow solid
  11. filtrationThe yellow solid is collected by filtration

출처 및 근거

ORD 기록
ord-cdd0b31e65d94423b494df186de21fa9
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977351B2

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