Potassium Phosphate, Tribasic → HCID 67222847, compound

HRID 2088741Notes

Reaction equation

HRID 2088741 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[I:13]C1C=CC=CN=1.CN[C@@H]1C[CH2:26][CH2:25][CH2:24][C@H:23]1[NH:28][CH3:29].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.O1CCOCC1>[I:13][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:29][N:28]=1)[CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2211262-IodopyridineHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 67222847HCID 67222847, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5 mL of 1,4-dioxane was added to 552 mg of 6-bromo-3,4-dihydroisoquinolin-1(2H)-one, 0.521 mL of 2-iodopyridine, 0.077 mL of trans-N,N′-dimethylcyclohexane-1,2-diamine and 622 mg of tripotassium phosphate, and stirred at 100° C. for 2 hours. Ethyl acetate was added to the reaction liquid, washed with aqueous saturated ammonia solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 582 mg of a mixture (1/1) of the entitled compound with 6-iodo-2-pyridin-2-yl-3,4-dihydroisoquinolin-1(2H)-one as a white solid.

Workup

  1. washwashed with aqueous saturated ammonia solution and saturated saline water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe solvent was evaporated away
  4. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-35a0f70d2aa945c9808d63a7ac60fa08
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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