Pyridine → HCID 11566254, compound

HRID 735416Notes

Reaction equation

HRID 735416 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1>C(Cl)Cl>[C:20]1([N:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:15]3[C:10]([C:11]([C:16]([F:18])([F:19])[F:17])=[CH:12][CH:13]=[CH:14]3)=[N:9]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 178506098HCID 178506098, compound

Product 1

HCID 11566254HCID 11566254, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Phenyl-7-trifluoromethylindazole (0.2 g, 0.76 mmol), phenyl boronic acid (186 mg, 1.53 mmol), copper II acetate (208 mg, 1.14 mmol), and pyridine (93 uL, 1.14 mmol) in 6 mL methylene chloride were stirred at room temperature for 72 hours. The reaction mixture was filtered through Celite®, poured into NH4Cl (sat. soln.) and extracted with EtOAc. The combined organic layers were dried with Na2SO4, concentrated and the resulting residue was purified by HPLC (10-100% CH3CN—H2O) to provide the desired compound as a white solid (40 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. additionpoured into NH4Cl (sat. soln.)
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. concentrationconcentrated
  6. customthe resulting residue was purified by HPLC (10-100% CH3CN—H2O)

Sources & evidence

ORD record
ord-a851e2919ded479bbea1641a76bccf37
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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