Boron tribromide → 6-chloro-1-(4-fluorophenyl)-1H-indazol-5-ol

HRID 13119Notes

Reaction equation

HRID 13119 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:18]C)=[C:14]([Cl:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[N:9][N:8]2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:12][C:13]=1[OH:18]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 593398871-(4-Fluorophenyl)-6-chloro-5-methoxy-1H-indazole

Product 1

HCID 593396696-chloro-1-(4-fluorophenyl)-1H-indazol-5-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Fluorophenyl)-6-chloro-5-methoxy-1H-indazole (99d) (0.91 mmol, 253 mg) was dissolved in dichloromethane (4 mL) and BBr3 (4 mL, 1 M/CH2Cl2) was added. The reaction mixture was stirred in room temperature overnight before it was quenched with water (20 mL). The product was extracted with dichloromethane (2×20 mL) and washed with sat NaHCO3. The organic phase was dried over Na2SO4, concentrated and purified by flash chromatography on silica gel (heptane-ethyl acetate). Yield: 219 mg (91%).

Workup

  1. customwas quenched with water (20 mL)
  2. extractionThe product was extracted with dichloromethane (2×20 mL)
  3. washwashed
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (heptane-ethyl acetate)

Sources & evidence

ORD record
ord-c66b0e81efe84e8996a9866222bb5056
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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