HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

HCID 67260634, compound → HCID 178510668, compound

HRID 2359052
Notes
Print preview

Reaction equation

HRID 2359052 reaction equation
Br[C:2]1[N:6](CC2C=CC(OC)=CC=2)[N:5]=[C:4]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[C:3]=1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.Br[C:29]1C(C2C=CN=CC=2)=C(C2SC(Cl)=CC=2)N(CC2C=CC(OC)=CC=2)[N:30]=1>CN(C)C=O.O.C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:21][C:18]1[S:17][C:16]([C:4]2[C:3]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)=[C:2]([C:29]#[N:30])[NH:6][N:5]=2)=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 2

HCID 67260634HCID 67260634, compoundHCID 67261945HCID 67261945, compound

Product 1

HCID 178510668HCID 178510668, compoundYield 15%

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To 4-[5-bromo-3-(5-chloro-2-thienyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine and 4-[3-bromo-5-(5-chloro-2-thienyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine (mixture of isomers 2:1, 1 eq, 0.435 mmol) in 1 mL of N,N-dimethylformamide, were added zinc cyanide (0.65 mmol) and Tetrakis(triphenylphosphine)palladium(0) (0.09 mmol). The mixture was stirred for 5 mins at 160° C. in the microwave. After cooling to room temperature, the reaction mixture was diluted with water and ethyl acetate was added. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was dissolved in 1 mL of trifluoroacetic acid and stirred at 65° C. for 2 h. Water and ethyl acetate were added. And the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with a saturated solution of sodium hydrogen carbonate, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane/methanol 20:1 to 10:1) to afford 19 mg of 3-(5-chloro-2-thienyl)-4-(pyridin-4-yl)-1H-pyrazole-5-carbonitrile (15% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 1 mL of trifluoroacetic acid
  8. stirringstirred at 65° C. for 2 h
  9. additionWater and ethyl acetate were added
  10. extractionAnd the aqueous layer was extracted with ethyl acetate
  11. washThe combined organic extracts were washed with a saturated solution of sodium hydrogen carbonate
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol 20:1 to 10:1)

Sources & evidence

ORD record
ord-9bfa95ee76a742ffbf4fb36da4001a09
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08685974B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes