Potassium Carbonate → 1-{[6-Chloro-1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(4-fluorophenyl)acetone

HRID 13118Notes

Reaction equation

HRID 13118 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.BrBr.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[N:20][N:21]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:17][C:16]=1[OH:31].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C1COCC1>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[N:20][N:21]2[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[CH:17][C:16]=1[O:31][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9]([CH3:10])=[O:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24408BromineHCID 521187(4-Fluorophenyl)acetoneHCID 593396696-chloro-1-(4-fluorophenyl)-1H-indazol-5-ol

Product 1

HCID 593396341-{[6-Chloro-1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(4-fluorophenyl)acetoneYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Fluorophenylacetone (388 μl, 2.9 mmol) in DCM (12 ml) was cooled to 0° C. and bromine (672 mg, 2.9 mmol) was slowly added. The mixture was stirred for 30 min and then concentrated in vacuo. The crude intermediate was added to a mixture of 6-chloro-1-(4-fluorophenyl)-1H-indazol-5-ol, (99c) (762 mg, 2.9 mmol) and potassium carbonate (804 mg, 5.8 mmol) in THF (12 ml). The mixture was stirred for 4 h, filtrated and concentrated. The crude product was purified by flash chromatography (EtOAc/heptane, product eluted at 40% EtOAc) to give the title compound (1.06 g, 88%).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe mixture was stirred for 4 h
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (EtOAc/heptane, product eluted at 40% EtOAc)

Sources & evidence

ORD record
ord-9a7f72306ac34c61a2b593cc65f0043a
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

Loading…