Methyl propiolate → 3-{5-[2-(2-Methyl-[1,8]naphthyridin-3-yl)-ethyl]-indol-1-yl}-acrylic acid methyl ester

HRID 24040

反応式

HRID 24040 の反応式
[CH3:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([Si](C(C)C)(C(C)C)C(C)C)[CH:18]=[CH:17]3)=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:33][O:34][C:35](=[O:38])[C:36]#[CH:37].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:33][O:34][C:35](=[O:38])[CH:36]=[CH:37][N:19]1[C:20]2[C:16](=[CH:15][C:14]([CH2:13][CH2:12][C:11]3[C:2]([CH3:1])=[N:3][C:4]4[C:9]([CH:10]=3)=[CH:8][CH:7]=[CH:6][N:5]=4)=[CH:22][CH:21]=2)[CH:17]=[CH:18]1

参加物

4

反応物 3

HCID 13536Methyl propiolateHCID 2724141Tetrabutylammonium FluorideHCID 225702682-methyl-3-[2-(1-triisopropylsilanyl-1H-indol-5-yl)-ethyl]-[1,8]naphthyridine

生成物 1

HCID 668213693-{5-[2-(2-Methyl-[1,8]naphthyridin-3-yl)-ethyl]-indol-1-yl}-acrylic acid methyl ester収率 66%

実験手順

A mixture of 2-methyl-3-[2-(1-triisopropylsilanyl-1H-indol-5-yl)-ethyl]-[1,8]naphthyridine (0.25 g, 0.74 mmol), propynoic acid methyl ester (0.07 g, 0.84 mmol), and tetrabutylammonium fluoride [1.0 M] (2.23 mL, 2.23 mmol) was stirred at room temperature overnight. The solvent was removed under reduced pressure to give a crude mixture which was purified via column chromatography with silica gel, eluting with methylene chloride/methanol (95/5) to give the title compound (66% yield) as an E/Z isomeric mixture. 1H NMR (CDCl3) δ 9.00 (m, 1H), 8.23 (s, 1H), 8.08 (m, 1H), 7.80 (m, 1H), 7.50 (d, 1H). Mass Spectrum (LCMS, ESI) calculated for C22H22N3O2 372.2 (M+H); found 372.2.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customto give a crude mixture which
  3. customwas purified via column chromatography with silica gel
  4. washeluting with methylene chloride/methanol (95/5)

出典と根拠

ORDレコード
ord-5295c85a8b2c4c4dba4df1e47b34415b
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

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