Potassium Phosphate, Tribasic → HCID 56940975, compound

HRID 1843946Notes

Reaction equation

HRID 1843946 reaction equation
[CH2:1]([N:3]1[C:15]2[C:14](=[O:16])[NH:13][CH:12]([CH3:17])[CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].I[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[CH3:25].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[CH2:1]([N:3]1[C:15]2[C:14](=[O:16])[N:13]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[CH:12]([CH3:17])[CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 144235133-Iodo-4-methylpyridineHCID 66803626HCID 66803626, compound

Product 1

HCID 56940975HCID 56940975, compoundYield 4.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

9-Ethyl-3-methyl-2,3,4,9-tetrahydro-b-carbolin-1-one (I-42d: 0.150 g, 0.657 mmol) was reacted with 3-iodo-4-methyl-pyridine (0.144 g, 0.657 mmol), K3PO4 (0.348 g, 1.644 mmol), CuI (0.012 g, 0.065 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (0.028 g, 0.197 mmol) and 1,4-dioxane (15 mL). The resulting mixture was heated at 120° C. for 23 hours to afford the crude product. Purification by column chromatography on silica gel (30% ethyl acetate in hexane) followed by preparative HPLC afforded 9 mg of the product (4.3% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-34f150e17c434526b902b9b5edbc65f9
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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