Potassium Carbonate → HCID 86692570, compound

HRID 1748632Notes

Reaction equation

HRID 1748632 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH2:16])=[O:15].Br[C:18]1[CH:19]=[CH:20][C:21]([C:24]2([C:34]#[N:35])[CH2:33][CH2:32][C:27]3([O:31][CH2:30][CH2:29][O:28]3)[CH2:26][CH2:25]2)=[N:22][CH:23]=1.CN(CC)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I.O>[C:34]([C:24]1([C:21]2[N:22]=[CH:23][C:18]([NH:16][C:14]([C:3]3[CH:4]=[N:5][N:6]([C:7]4[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=4)[C:2]=3[CH3:1])=[O:15])=[CH:19][CH:20]=2)[CH2:25][CH2:26][C:27]2([O:28][CH2:29][CH2:30][O:31]2)[CH2:32][CH2:33]1)#[N:35]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11723DimethylethylamineHCID 8080138HCID 8080138, compoundHCID 86692457HCID 86692457, compound

Product 1

HCID 86692570HCID 86692570, compoundYield 2.6%

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

5-Methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxamide (786 mg) and 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.12 g) described in Reference Example 82, copper (I) iodide (35 mg), N,N-dimethylethylamine (33 mg) and potassium carbonate in 1,4-dioxane (5 ml) was stirred at 100° C. for six hours. After 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 a silica gel column chromatography to give the titled compound (42 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 a silica gel column chromatography

Sources & evidence

ORD record
ord-7c0cd5129d224ed8b6c92092a080f973
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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