Hydrochloric Acid → 5-chloro-2-(4-chlorophenyl)-1H-Indole

HRID 1016647

反応式

HRID 1016647 の反応式
C([Li])CCC.[Cl:6][C:7]1[CH:23]=[CH:22][C:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[CH3:21])=O)=[CH:9][CH:8]=1.Cl>O1CCCC1>[Cl:20][C:17]1[CH:16]=[C:15]2[C:14](=[CH:19][CH:18]=1)[NH:13][C:11]([C:10]1[CH:22]=[CH:23][C:7]([Cl:6])=[CH:8][CH:9]=1)=[CH:21]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 2952414,4'-Dichloro-2'-methylbenzanilideHCID 178418339Butyllithium2 回

生成物 1

HCID 140455245-chloro-2-(4-chlorophenyl)-1H-Indole収率 14.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

n-Butyllithium (1.6M in hexanes, 127 mL, 203 mmol) was added dropwise to a stirred, cooled (−10° C.) solution of 4-chloro-N-(4-chloro-2-methylphenyl)benzamide (Description 27, 27.1 g, 97 mmol) in tetrahydrofuran (600 mL). The mixture was allowed to warm to room temperature and stirred overnight. The mixture was cooled to 0° C. and further n-butyllithium (1.6M in hexanes, 30 mL, 483 mmol) was added dropwise. The mixture was stirred at room temperature for 2 h., then hydrochloric acid (2.5M, 200 mL) was added. The mixture was stirred at room temperature overnight, then extracted with ethyl acetate. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (85:15), to give the title compound (3.6 g, 14%). 1H NMR (360 MHz, CDCl3) δ 8.30 (1H, br s), 7.57 (3H, m), 7.42 (2H, d, J 9.1 Hz), 7.30 (1H, d, J 8.6 Hz), 7.15 (1H, dd, J 8.6, 2.0 Hz) and 6.74 (1H, s).

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred at room temperature for 2 h.
  3. stirringThe mixture was stirred at room temperature overnight
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic fractions were dried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with isohexane/EtOAc (85:15)

出典と根拠

ORDレコード
ord-d878602752ca400ca0ebc28fe63db989
出典データセット
uspto-grants-2002_11
特許番号
US06476045B2

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