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

HRID 489558노트

반응식

HRID 489558 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-93c5a6665a9a41b78361226cfcc3d8fc
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977298B2

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