Potassium Carbonate → HCID 90391302, compound

HRID 1486588Notes

Reaction equation

HRID 1486588 reaction equation
Br[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13]2[N:17]=[C:16]([NH2:18])[NH:15][N:14]=2)=[CH:4][C:3]=1[Cl:19].[CH:20]([S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24])([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+]>COCCOC.O1CCOCC1.CO.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:19][C:3]1[CH:4]=[C:5]([NH:12][C:13]2[N:17]=[C:16]([NH2:18])[NH:15][N:14]=2)[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]=1[C:29]1[CH:28]=[CH:27][C:26]([S:23]([CH:20]([CH3:22])[CH3:21])(=[O:25])=[O:24])=[CH:31][CH:30]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 441193274-(Isopropylsulphonyl)benzeneboronic acidHCID 72714613HCID 72714613, compound

Product 1

HCID 90391302HCID 90391302, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of N3-(4-bromo-3-chloro-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 1 (150 mg, 421 μmol), 4-(isopropylsulfonyl)phenylboronic acid (240 mg, 1.05 mmol) and 3M K2CO3 (351 μl, 1.05 mmol) in DME (1 ml) and dioxane (1 ml) was degassed with argon and tetrakis(triphenylphosphine)palladium(0) (97.2 mg, 84.1 μmol) was added. The reaction mixture was heated in microwave at 125° C. for 3 hours, diluted with MeOH, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 24 g, 3% to 7% MeOH in DCM). Further purification by super fluid chromatography afforded a white foam (32 mg, 16% yield) as desired product. MS +m/z: 460 (M+H)+

Workup

  1. additionwas added
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (silica gel, 24 g, 3% to 7% MeOH in DCM)
  5. customFurther purification by super fluid chromatography

Sources & evidence

ORD record
ord-d149905976654a7294b9756520ca00a3
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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