Methyl triflate → HCID 10836559, compound

HRID 582670Notes

Reaction equation

HRID 582670 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[S:14][C:3]=12.[CH3:19][O:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22]>C1(C)C=CC=CC=1>[F:25][C:24]([F:27])([F:26])[S:21]([O-:23])(=[O:22])=[O:20].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]([CH3:19])=[C:4]2[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[S:14][C:3]=12

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 1084961135771-74-5

Product 1

HCID 10836559HCID 10836559, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 11-chlorobenzothieno[3,2b]quinoline from Example 60 (0.16 g; 0.06 mmol) in 12 mL of toluene was added MeOTf (0.081 mL, 120 mol %) and the reaction mixture was stirred at rt for 20 h. The resulting crystalline yellow product was filtered, triturated with EtOAc for 24 h, filtered and dried, providing the title compound (38%), mp 187-189° C.; 1H NMR (DMSO-d6) δ 9.00 (d, 1H, J=8.4), 8.97 (d, 1H, J=8.2), 8.67 (d, 1H, J=8.4), 8.51 (d, 1H, J=8.4), 8.21-7.89 (m, 4H); 13C NMR (DMSO-d6) δ 148.34, 143.68, 143.11, 139.34, 135.72, 133.95, 130.59, 130.08, 128.35, 127.10, 125.12, 124.89, 119.88, 42.79; MS (+FAB, m/z) 284 (M+) MS (-FAB, m/z) 149.

Workup

  1. filtrationThe resulting crystalline yellow product was filtered
  2. customtriturated with EtOAc for 24 h
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-2baad8e27b4e4a3998d7da97a2d4b07b
Source dataset
uspto-grants-1999_07
Patent number
US05925647

Reaction notes

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