5-Bromonicotinamide → HCID 86692599, compound

HRID 1748658Notes

Reaction equation

HRID 1748658 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=[O:9])[CH:5]=[N:6][CH:7]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C:28]#[N:29])[CH2:27][CH2:26][C:21]3([O:25][CH2:24][CH2:23][O:22]3)[CH2:20][CH2:19]2)=[N:16][CH:17]=1.CN(CC)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I.O>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:3]=1)[C:8]([NH:10][C:12]1[CH:17]=[N:16][C:15]([C:18]2([C:28]#[N:29])[CH2:27][CH2:26][C:21]3([O:22][CH2:23][CH2:24][O:25]3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)=[O:9]

Participants

8

Reactant 4

HCID 18085-BromonicotinamideHCID 11430Potassium CarbonateHCID 11723DimethylethylamineHCID 86692457HCID 86692457, compound

Product 1

HCID 86692599HCID 86692599, compoundYield 13.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-bromopyridine-3-carboxamide (734 mg), 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.18 g) described in Reference Example 82, copper (I) iodide (35 mg), N,N-dimethylethylamine (33 mg) and potassium carbonate (1.01 g) in 1,4-dioxane (5 ml) was stirred at 100° C. for six hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography to give 5-bromo-N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]nicotinamide (213 mg).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified with column chromatography

Sources & evidence

ORD record
ord-e15b4671fc7d41f3babb3d777d452c6f
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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