Water → HCID 117988445, compound

HRID 2206078Notes

Reaction equation

HRID 2206078 reaction equation
FC(F)(F)S(O[C:7]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[N:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[CH:20][CH:19]=2)[N:8]=1)(=O)=O.[C:30]1(B2OC(C)(C)C(C)(C)O2)[CH2:34][CH2:33][CH2:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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>[C:30]1([C:7]2[C:15]3[C:10](=[C:11]([O:16][CH3:17])[N:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([NH2:25])(=[O:27])=[O:26])=[CH:20][CH:19]=3)[N:8]=2)[CH2:34][CH2:33][CH2:32][CH:31]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 117987820HCID 117987820, compound

Product 1

HCID 117988445HCID 117988445, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 7-methoxy-1-(4-sulfamoylphenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl trifluoromethanesulfonate (59 mg), 2-(cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (25.3 mg), tetrakis(triphenylphosphine)palladium(0) (7.5 mg) and 2M aqueous sodium carbonate solution (0.33 mL) in DME (5 mL) was stirred under argon atmosphere at 100° C. for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (22 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bcbc6ee0f7b1455c9ae2618d49f178e2
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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