Water → Indole

HRID 493246

反応式

HRID 493246 の反応式
C(OC([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Cl)=[CH:10][CH:9]=2)=O)C.[H-].[Na+].C1(S(Cl)(=O)=O)C=CC=CC=1.O>CN(C=O)C>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:6]1

参加物

6

反応物 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 78518Ethyl 5-chloroindole-2-carboxylate

生成物 1

HCID 798Indole収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred and cooled (0° C.) solution of ethyl-5-chloroindole-2-carboxylate (1.052 g, 4.70 mmol) in DMF (25 mL) under N2, was added NaH (60% in oil, 230 mg, 5.64 mmol) portionwise. After the end of gas evolution, phenylsulfonyl chloride (0.72 mL, 5.64 mmol) was added. The reaction mixture was stirred for 1H (TLC monitoring, eluant dichloromethane). A little amount of water was added carefully and DMF was evaporated. Crude residue was dissolved in EtOAc and washed with water and brine. After drying and evaporation of solvents the compound was purified by chromatography on silica gel (eluant:cyclohexane/EtOAc 9/1 to 7/3) to afford protected indole (1.547 g, 90% yield. Off-white solid; 1H NMR (d6-DMSO) δ 1.30 (t, J=7.2 Hz, 3H), 4.35 (q, J=7.2 Hz, 2H), 7.37 (s, 1H), 7.53 (dd, J=2.2 and 9.1 Hz), 7.62-7.77 (m, 3H), 7.80 (d, J=2.2 Hz, 1H), 7.99 (m, 2H), 8.06 (d, J=9.1 Hz); MS (ESI, E1+) m/z=364 (MH+).

後処理

  1. stirringThe reaction mixture was stirred for 1H (TLC monitoring, eluant dichloromethane)
  2. customDMF was evaporated
  3. dissolutionCrude residue was dissolved in EtOAc
  4. washwashed with water and brine
  5. customAfter drying
  6. customevaporation of solvents the compound
  7. customwas purified by chromatography on silica gel (eluant:cyclohexane/EtOAc 9/1 to 7/3)

出典と根拠

ORDレコード
ord-9e7234c161884d3287fe94a865fee2fa
出典データセット
uspto-grants-2009_05
特許番号
US07534809B2

関連ノート

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