1,2,3,4-Tetrahydroisoquinoline → HCID 67042131, compound

HRID 1405508Notes

Reaction equation

HRID 1405508 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH2:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][NH:23]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][N:23]1[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 67042131HCID 67042131, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Into a 8-mL sealed tube, was placed a solution of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (130 mg, 0.38 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL), 1,2,3,4-tetrahydroisoquinoline (101.1 mg, 0.76 mmol, 2.00 equiv), potassium carbonate (157.3 mg, 1.14 mmol, 3.00 equiv). The resulting solution was stirred for overnight at 100° C. The reaction was then quenched by the addition of water. The resulting solids were collected by filtration. This resulted in 110 mg (70%) of methyl 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customInto a 8-mL sealed tube
  2. customThe reaction was then quenched by the addition of water
  3. filtrationThe resulting solids were collected by filtration
  4. customThis resulted in 110 mg (70%) of methyl 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylquinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-a39f61c6d6cc46e9bea0c39ddd853491
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

Loading…