Potassium Phosphate, Tribasic → HCID 56940973, compound

HRID 1843922Notes

Reaction equation

HRID 1843922 reaction equation
[CH2:1]([N:3]1[C:15]2[C:14](=[O:16])[NH:13][CH2:12][CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].I[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH2:1]([N:3]1[C:15]2[C:14](=[O:16])[N:13]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[CH3:24])[CH2:12][CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 66803551HCID 66803551, compound

Product 1

HCID 56940973HCID 56940973, compoundYield 13.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

9-Ethyl-2,3,4,9-tetrahydro-b-carbolin-1-one (I-38f: 0.1 g, 0.4672 mmol) was reacted with 3-iodo-4-methyl-pyridine (0.102 g, 0.4672 mmol), 1,4-dioxane (15 mL), copper iodide (0.0089 g, 0.0467 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (0.019 g, 0.01401 mmol) and potassium phosphate (0.247 g, 1.168 mmol) to afford the crude product. Purification by column chromatography on silica gel (70% ethylacetate in hexane), followed by preparative HPLC afforded 0.019 g of the product (13.3% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (70% ethylacetate in hexane)

Sources & evidence

ORD record
ord-b7985d7b5fac43deacd25f222d826db7
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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