Methyl triflate → HCID 86751476, compound

HRID 582682Notes

Reaction equation

HRID 582682 reaction equation
[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

Participants

5

Reactant 2

HCID 9526Methyl triflateHCID 178477809HCID 178477809, compound

Product 1

HCID 86751476HCID 86751476, compoundYield 279.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

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 1 M 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+).

Workup

  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

Sources & evidence

ORD record
ord-c4fcb9546f8a411e979a70516d613d48
Source dataset
uspto-grants-1999_07
Patent number
US05925647

Reaction notes

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