Water → HCID 117988210, compound

HRID 2206066Notes

Reaction equation

HRID 2206066 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[NH:10][N:11]=[C:12]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:3]=12.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[S:29][CH:30]=2)O1.N1C=CC=CC=1.O>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[N:10]([C:26]3[CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[S:29][CH:30]=3)[N:11]=[C:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[C:3]=12

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 52911233Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylateHCID 178494031HCID 178494031, compound

Product 1

HCID 117988210HCID 117988210, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-bromo-3-cyclopentyl-7-methoxy-1H-pyrazolo[3,4-c]pyridine (100 mg), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (181 mg), copper(II) acetate (73.6 mg) and pyridine (37.4 mg) in DMF (10 mL) was stirred at room temperature for 4 days. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 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 (65 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  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-7fcec29045c246ddb35a62bf5779a3d6
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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