Ethyl Acetate → Lxr-623

HRID 735439Notes

Reaction equation

HRID 735439 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH2:24]Br.C(OCC)(=O)C>CN(C=O)C>[Cl:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH2:24][N:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:16]2[C:11]([C:12]([C:17]([F:18])([F:20])[F:19])=[CH:13][CH:14]=[CH:15]2)=[N:10]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzeneHCID 178505585HCID 178505585, compound

Product 1

HCID 16734800Lxr-623Yield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(4-fluoro-phenyl)-7-trifluoromethyl-1H-indazole (6.43 g, 23 mmol) in 20 mL DMF was added 2-chloro-4-fluoro benzyl bromide (7.0 g, 31 mmol). The reaction mixture was heated overnight at 120° C. After cooling to room temperature, ethyl acetate was added and the solution was washed three times with brine. The organic layer was dried over NaSO4 and concentrated. Flash chromatography (hexane/CH2Cl2, 1:1, as eluent) afforded 4.1 g of pure product. Three grams (3 g) of product were recrystallized from 10 mL of isopropanol to recover 1.98 g of crystalline product, mp 78° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe solution was washed three times with brine
  3. dry with materialThe organic layer was dried over NaSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-297433edd05f4d8889aaec15a6c4cb48
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

Loading…