Methyl triflate → HCID 86751470, compound

HRID 1490300Notes

Reaction equation

HRID 1490300 reaction equation
[Cl:1][C:2]1[C:18]2[C:17]([Cl:19])=[C:16]3[C:8](=[C:9]4[C:14](=[N:15]3)[CH:13]=[CH:12][CH:11]=[CH:10]4)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:20]OS(C(F)(F)F)(=O)=O>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[C:18]2[C:17]([Cl:19])=[C:16]3[C:8](=[C:9]4[C:14](=[N:15]3)[CH:13]=[CH:12][CH:11]=[CH:10]4)[NH+:7]([CH3:20])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9526Methyl triflate2×HCID 178477988HCID 178477988, compound

Product 1

HCID 86751470HCID 86751470, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of 1-chloro-11-chloroquindoline from Example 50 (0.3 g, 1.0 mmol) in anhydrous toluene (12 mL) was added methyltriflate (0.25 mL, 200 mol %). The reaction mixture was stirred for 20 h at rt after which TLC analysis still showed starting material. Additional methyl triflate (100 mol %) and toluene (5 mL) were added. The reaction mixture was stirred overnight, filtered, washed with ether and dried to afford the crude title compound; MS (-FAB, m/z) 149.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationfiltered
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-a7d5f525e2b84d72ae63292f34a17ed6
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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