3-Bromopyridine → HCID 56940974, compound

HRID 1843932Notes

Reaction equation

HRID 1843932 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].Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.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:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[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

6

Reactant 3

HCID 122863-BromopyridineHCID 62657Potassium Phosphate, TribasicHCID 66803626HCID 66803626, compound

Product 1

HCID 56940974HCID 56940974, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 9-ethyl-3-methyl-2,3,4,9-tetrahydro-b-carbolin-1-one (I-42d: 0.1 g, 0.4386 mmol) was reacted with 3-bromo-pyridine (0.069 g, 0.4386 mmol), 1,4-dioxane (15 mL), copper iodide (0.008 g, 0.0438 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (0.018 mg, 0.1315 mmol) and potassium phosphate (0.232 g, 1.096 mmol) to afford the crude product. Purification by column chromatography on silica gel (70% ethylacetate in hexane) afforded 46 mg of the product (34% yield).

Workup

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

Sources & evidence

ORD record
ord-a237e8607bf844c3bbbdde14e2e8f50e
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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