Potassium Phosphate, Tribasic → HCID 56943049, compound

HRID 1843952Notes

Reaction equation

HRID 1843952 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:9]=2)[C:4](=[O:16])[NH:3]1.I[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([C:12]([F:13])([F:15])[F:14])=[CH:8][CH:9]=2)[C:4](=[O:16])[N:3]1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 144235133-Iodo-4-methylpyridineHCID 66801674HCID 66801674, compound

Product 1

HCID 56943049HCID 56943049, compoundYield 3.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

3-Methyl-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one (I-43d: 200 mg, 0.872 mmol) was reacted with 3-iodo-4-methyl-pyridine (287 mg, 1.308 mmol), K3PO4 (463 mg, 2.18 mmol), trans-N,N′-dimethyl-cyclohexane-1, 2-diamine (40 mg), CuI (20 mg) and 1,4-dioxane (5 mL). The resulting mixture was refluxed for 64 hours at 110° C. to afford the crude product. Purification by column chromatography on silica gel (90% ethylacetate in hexane) followed by preparative HPLC afforded 10 mg of the product (3.58% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (90% ethylacetate in hexane)

Sources & evidence

ORD record
ord-bddf7ce2eaa74551a1f03a88d23cabae
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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