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

HRID 8340

反応式

HRID 8340 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A mixture of butylmagnesium chloride (1 mL, Immol, 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, 3 H), 7.60–7.35 (m, 3 H), 7.19 (t, J=8 Hz, 1 H), 6.98 (s, 1 H), 6.72 (d, J=8 Hz, 1 H), 3.62 (m, 4 H), 3.05 (m, 4 H), 1.47 (m, 9 H); MS (ESI+) for m/z 568 (M+H)+.

後処理

  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 100 mg (35%)

出典と根拠

ORDレコード
ord-5f7ad1a822044384bf271b2d527fe775
出典データセット
uspto-grants-2006_08
特許番号
US07087750B2

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