Methyl triflate → HCID 86751476、化合物

HRID 1490320ノート

反応式

HRID 1490320 の反応式
[Cl:1][C:2]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:12][C:11]2[C:3]=1[N:4]=[C:5]1[C:10]=2[CH:9]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[CH:6]1.O(C)S([C:29](F)(F)F)(=O)=O>C1(C)C=CC=CC=1.C(OCC)C>[ClH:1].[Cl:1][C:2]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH+:12]([CH3:29])[C:11]2[C:3]=1[N:4]=[C:5]1[C:10]=2[CH:9]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[CH:6]1

参加物

5

反応物 2

HCID 9526Methyl triflateHCID 178477809HCID 178477809、化合物

生成物 1

HCID 86751476HCID 86751476、化合物収率 279.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 11-chloro-7-phenylquindoline from Example 96 (0.250 g, 0.760 mmol) in toluene (10 ml, freshly distilled) stirring under nitrogen was added methyl triflate (0.130 mL, 0.114 mmol). The mixture stirred for 2 h at room temperature and was diluted with diethyl ether (40 mL) and filtered. The orange filter cake was placed under high vacuum for 24 h. The orange residue was suspended in chloroform and adsorbed onto neutral alumina. The adsorbent was chromatographed over basic alumina (eluting with chloroform until the eluant was free of impurities by TLC, then eluting with 0.2% methanol in chloroform). The violet fractions were collected and concentrated to a small volume (50 mL). The violet solution was acidified with ethereal 1M HCl to a bright yellow endpoint. The mixture was cooled below room temperature and filtered. The filter cake was dried under high vacuum to yield 0.121 g (42%) of the title compound as a red solid; 1H NMR (DMSO-d6) δ 13.62 (s, 1H), 8.90-8.86 (m, 2H), 8.60 (d, J=8.4, 1H), 8.27-8.20 (m, 2H), 8.06 (t, J=7.6, 1H), 7.92-7.88 (m, 3H), 7.55 (t, J=7.6, 2H), 7.44 (t, J=7.6, 1H), 5.11 (s, 3H); 13C NMR (DMSO- d6) δ 145.21, 139.37, 138.58, 135.80, 134.31, 133.73, 132.84, 132.04, 129.10, 129.00, 128.39, 127.55, 127.28, 126.96, 126.62, 124.55, 123.80, 123.37, 118.82, 114.93, 113.91, 40.65; MS (FAB, m/z) 343 (M+).

後処理

  1. stirringThe mixture stirred for 2 h at room temperature
  2. filtrationfiltered
  3. customThe adsorbent was chromatographed over basic alumina (
  4. washeluting with chloroform until the eluant
  5. washeluting with 0.2% methanol in chloroform)
  6. customThe violet fractions were collected
  7. concentrationconcentrated to a small volume (50 mL)
  8. temperatureThe mixture was cooled below room temperature
  9. filtrationfiltered
  10. customThe filter cake was dried under high vacuum

出典と根拠

ORDレコード
ord-acb1d819ddd74e9a9fdd0400b6cb38ae
出典データセット
uspto-grants-1997_10
特許番号
US05681958

反応ノート

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