Potassium Phosphate, Tribasic → HCID 90031463, compound

HRID 624666Notes

Reaction equation

HRID 624666 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.Br[C:15]1[N:19]([CH3:20])[CH:18]=[N:17][CH:16]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH3:20][N:19]1[C:15]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]2)=[CH:16][N:17]=[CH:18]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 589098Methyl indole-3-carboxylateHCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 90031463HCID 90031463, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of methyl 1H-indole-3-carboxylate (300 mg, 1.712 mmol) and 5-bromo-1-methyl-1H-imidazole (303 mg, 1.884 mmol) in toluene (3425 μl) was treated with (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (82 μl, 0.514 mmol), potassium phosphate (763 mg, 3.60 mmol) and copper(I) iodide (98 mg, 0.514 mmol) and the resulting reaction mixture stirred at 110° C. overnight. HPLC purification afforded the title compound as a yellow solid.

Workup

  1. customthe resulting reaction mixture
  2. customHPLC purification

Sources & evidence

ORD record
ord-b9e5fbb99bab498a941d43484e7537d3
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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