Iodine → 1-Piperazinecarboxylic acid,4-[2-iodo-1-(phenylsulfonyl)-1h-indol-4-yl]-,1,1-dimethylethyl ester

HRID 2112466

반응식

HRID 2112466 반응식
C([Mg]Cl)CCC.C(NC(C)C)(C)C.[C:14]1([S:20]([N:23]2[C:31]3[C:26](=[C:27]([N:32]4[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]4)[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[I:45]I>C1COCC1>[I:45][C:24]1[N:23]([S:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:22])=[O:21])[C:31]2[C:26]([CH:25]=1)=[C:27]([N:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)[CH:28]=[CH:29][CH:30]=2

참가 물질

6

반응물 4

HCID 807IodineHCID 7912DiisopropylamineHCID 22015366t-butyl 4-(1-benzenesulfonyl-1H-indol-4-yl)piperazine-1-carboxylateHCID 178418265HCID 178418265, 화합물

생성물 1

HCID 220153301-Piperazinecarboxylic acid,4-[2-iodo-1-(phenylsulfonyl)-1h-indol-4-yl]-,1,1-dimethylethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A mixture of butylmagnesium chloride (1 mL, 1 mmol, 2.0 M in ether) and di-isopropyl amine (0.279 mL, 2 mmol) in dry THF (5 mL) was stirred for 4 h under inert atmosphere at room temperature. A solution of tert-butyl 4-[1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate (220 mg, 0.5 mmol) in THF (2 mL) was added slowly and the resulting mixture stirred for 2 h at room temperature. A solution of iodine (380 mg, 2.2 mmol) in THF (2 mL) was added dropwise and the mixture was stirred overnight. After evaporation of the solvent in vacuo, the residue was treated with an aqueous solution of NH4Cl (10 mL). The mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (SiO2) using CH2Cl2 as eluent to give, 100 mg (35%). 1H NMR (500 MHz, CDCl3) δ 8.05-7.80 (m, 3H), 7.60-7.35 (m, 3H), 7.19 (t, J=8 Hz, 1H), 6.98 (s, 1H), 6.72 (d, J=8 Hz, 1H), 3.62 (m, 4H), 3.05 (m, 4H), 1.47 (m, 9H); MS (ESI+) for m/z 568 (M+H)+.

후처리

  1. stirringthe resulting mixture stirred for 2 h at room temperature
  2. stirringthe mixture was stirred overnight
  3. customAfter evaporation of the solvent in vacuo
  4. additionthe residue was treated with an aqueous solution of NH4Cl (10 mL)
  5. extractionThe mixture was extracted with CH2Cl2 (3×10 mL)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (SiO2)
  9. customto give

출처 및 근거

ORD 기록
ord-284ebe223e234022a695fd4d27197980
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524839B2

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