Acetonitrile → HCID 67261632, compound

HRID 2359107Notes

Reaction equation

HRID 2359107 reaction equation
C(#N)C.C(=O)([O-])[O-].[K+].[K+].[Cl:10][C:11]1[S:15][C:14]([C:16]2[C:20](B3OC(C)(C)C(C)(C)O3)=[CH:19][N:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:17]=2)=[CH:13][CH:12]=1.Br[C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=[CH:37][CH:36]=1>O>[Cl:10][C:11]1[S:15][C:14]([C:16]2[C:20]([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=[CH:37][CH:36]=3)=[CH:19][N:18]([CH2:30][CH:31]([CH3:32])[CH3:33])[N:17]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 117359184-bromoquinolineHCID 67389116HCID 67389116, compound

Product 1

HCID 67261632HCID 67261632, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a degassed solution of acetonitrile (4 mL) and water (1 mL) were added potassium carbonate (4 eq, 2.8 mmol), 3-(5-chloro-2-thienyl)-1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 eq, 0.7 mmol), 4-bromoquinoline (1 eq, 0.7 mmol) and 1,1′-bis(diphenylphosphinoferrocene)palladium(II)dichloride (0.1 eq, 0.07 mmol). The mixture was stirred at 130° C. in the microwave for 60 min. The solvent was evaporated and water and dichloromethane were added. The aqueous layer was extracted two times with dichloromethane. The combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol 1:0 to 9:1) to afford 45 mg of 4-[3-(5-chloro-2-thienyl)-1-isobutyl-1H-pyrazol-4-yl]quino line (15% yield).

Workup

  1. customThe solvent was evaporated
  2. additionwater and dichloromethane were added
  3. extractionThe aqueous layer was extracted two times with dichloromethane
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol 1:0 to 9:1)

Sources & evidence

ORD record
ord-f846dc9e2b4d483d9be551ff66324b8c
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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