Ethanol → HCID 59334593, compound

HRID 1639868Notes

Reaction equation

HRID 1639868 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[CH:12]1[CH2:14][CH:13]1[CH2:15][NH:16][C:17](=[O:19])[CH3:18].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C(OCC)(=O)C.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.C1(C)C=CC=CC=1>[CH3:11][N:6]1[CH:5]=[C:4]2[C:8]([CH:9]=[CH:10][C:2]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:3]2[CH:12]2[CH2:14][CH:13]2[CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[N:7]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59334491HCID 59334491, compound

Product 1

HCID 59334593HCID 59334593, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N-{[2-(5-Bromo-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (100 mg, 0.310 mmol) obtained in Example 29, phenylboronic acid (94.6 mg, 0.776 mmol), 2 M aqueous sodium carbonate solution (3 mL) and tetrakis(triphenylphosphine)palladium(0) (35.8 mg, 0.031 mmol) were added to a mixed solution of ethanol (1.5 mL) and toluene (1.5 mL), and the mixture was stirred under nitrogen atmosphere with heating at 80° C. for 15 hr. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) to give the title compound (98.9 mg, yield 99%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90)

Sources & evidence

ORD record
ord-0a344b94be544e1e8823349d1f653862
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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