Methyl triflate → HCID 86751471, compound

HRID 1490302Notes

Reaction equation

HRID 1490302 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[O: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.CCOCC>[F:25][C:24]([F:27])([F:26])[S:21]([OH:23])(=[O:22])=[O:20].[Cl:1][CH: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[O:14][C:3]1=2

Participants

5

Reactant 2

HCID 9526Methyl triflateHCID 1075339869764-19-8

Product 1

HCID 86751471HCID 86751471, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 11-chlorobenzofuro[3, 2-b]quinoline from Example 55 (0.4 g, 1.6. mol) in anhydrous toluene (15 mL) was added methyltriflate (0.52 g, 0.36 mL, 200 mol %). The reaction mixture was stirred for 20 h at rt, diluted with ether, and stirred for 1 h. The solid product was filtered to afford after drying, 0.41 g (62%) of the title compound, mp 221°-223° C. (became "wet" at 200°-202° C.); 1H NMR (DMSO-d6) δ 8.90 (q, 2H, J=8), 8.73 (dd, 1H, J=1.2, J=8), 8.40-8.36 (m, 1H), 8.24-8.14 (m, 3H), 7.83 (m, 1H); 13C NMR (DMSO-d6) δ 159.53, 145.04, 142.89, 137.44, 136.69, 134.57, 130.32, 129.93, 127.05, 126.02, 125.43, 125.38, 124.73, 119.23, 116.62, 113.80, 106.93, 40.00; MS (FAB, m/z) 268 (M+).

Workup

  1. stirringstirred for 1 h
  2. filtrationThe solid product was filtered
  3. customto afford
  4. customafter drying
  5. custom0.41 g (62%) of the title compound, mp 221°-223° C. (became "wet" at 200°-202° C.)

Sources & evidence

ORD record
ord-aede897168e949f38812314d864027b0
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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