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Potassium Carbonate → HCID 86692570, compound

HRID 1748632
Notes
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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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 962WaterSolvent
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150555B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes