2-Propynoic acid, 3-phenyl-, ethyl ester → 3-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-3-phenyl-acrylic acid ethyl ester

HRID 24047

反応式

HRID 24047 の反応式
C([Si](C(C)C)(C(C)C)[N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][CH2:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)(C)C.[CH2:33]([O:35][C:36](=[O:45])[C:37]#[C:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:34].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:33]([O:35][C:36](=[O:45])[CH:37]=[C:38]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][CH2:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:34]

参加物

5

反応物 3

HCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 2724141Tetrabutylammonium FluorideHCID 225702802-[3-(1-triisopropylsilanyl-1H-indol-5-yl)-propyl]-[1,8]naphthyridine

生成物 1

HCID 668212473-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-3-phenyl-acrylic acid ethyl ester収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-[3-(1-triisopropylsilanyl-1H-indol-5-yl)-propyl]-[1,8]naphthyridine (125 mg, 0.282 mmol), phenyl-propynoic acid ethyl ester (98.0 mg, 0.563 mmol), and tetrabutylammonium fluoride [1.0 M] 0.85 mL, 0.85 mmol) in THF (3 mL) was stirred for 24 h. After removal of the solvent, the crude reaction mixture was purified via column chromatography on silica gel with ethyl acetate/hexane (2:1) to give the title product as an E/Z isomeric mixture in 64% yield. Mass Spectrum (LCMS, ESI) calculated for C30H28N3O2 462.2 (M+H); found 462.3.

後処理

  1. customAfter removal of the solvent
  2. customthe crude reaction mixture
  3. customwas purified via column chromatography on silica gel with ethyl acetate/hexane (2:1)

出典と根拠

ORDレコード
ord-9a7f4c5bc94e4e58bee518d15e7b3e6d
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

関連ノート

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