3-Amino-2-(4-chloro-phenylethynyl)-benzoic acid methyl ester → 2-(4-Chloro-phenyl)-1H-indole-4-carboxylic acid methyl ester

HRID 489558

反応式

HRID 489558 の反応式
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1>C(#N)C.[Pd](Cl)Cl>[CH3:1][O:2][C:3]([C:4]1[C:5]2[CH:11]=[C:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[NH:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:20]

参加物

4

反応物 1

HCID 183400043-Amino-2-(4-chloro-phenylethynyl)-benzoic acid methyl ester

生成物 1

HCID 183400022-(4-Chloro-phenyl)-1H-indole-4-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 6342Acetonitrile溶媒

実験手順

3-amino-2-(4-chloro-phenylethynyl)-benzoic acid methyl ester (0.73 g, 2.54 mmol) and palladium (II) chloride (23 mg, 0.13 mmol) were combined in 10 mL acetonitrile. The yellow solution was stirreed under argon at 75° C. for 17 h. The solvent was removed in vacuo leaving an orange solid which was purified by flash chromatography eluting with 50 to 100% CH—Cl3/hecanes. 2-(4-chloro-henyl)-1H-indole-4-carboxylic acid methyl ester; 0.53 g (72%) was isolated as an off-white solid: m.p. 150.0-151.5° C.; 1H NMR (300 MHz, d6-DMSO) δ 3.93 (s, 3H), 7.23 (app t, J=7.8 Hz, 1H), 7.41 (d, J=1.8 Hz, 1H), 7.57 (d, J=8.7 Hz, 2H), 7.68 (d, J=7.8 Hz, 1H), 7.75 (dd, J=7.5, 0.9 Hz, 1H), 7.95 (d, J=8.7 Hz, 2H), 11.99 (br s, 1H). HRMS (MALDI, MH+) Calcd for C16H12ClNO2: 286.0635. Found: 286.0631.

後処理

  1. customThe solvent was removed in vacuo
  2. customleaving an orange solid which
  3. customwas purified by flash chromatography
  4. washeluting with 50 to 100% CH—Cl3/hecanes
  5. custom0.53 g (72%) was isolated as an off-white solid

出典と根拠

ORDレコード
ord-93c5a6665a9a41b78361226cfcc3d8fc
出典データセット
uspto-grants-2005_12
特許番号
US06977298B2

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