Methyl triflate → HCID 86751476, 화합물

HRID 1490320노트

반응식

HRID 1490320 반응식
[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

참가 물질

5

반응물 2

HCID 9526Methyl triflateHCID 178477809HCID 178477809, 화합물

생성물 1

HCID 86751476HCID 86751476, 화합물수율 279.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-acb1d819ddd74e9a9fdd0400b6cb38ae
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05681958

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