Boron → 2-(3-chloro-4-fluoro-phenylamino)-N-(5-hydroxy-2-methyl-phenyl)-acetamide

HRID 1267923Notes

Reaction equation

HRID 1267923 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([O:20]C)[CH:17]=[CH:16][C:15]=2[CH3:22])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].[B]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=2[CH3:22])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 5462311BoronHCID 185424132-(3-Chloro-4-fluorophenylamino)-N-(5-methoxy-2-methylphenyl)-acetamide

Product 1

HCID 185423932-(3-chloro-4-fluoro-phenylamino)-N-(5-hydroxy-2-methyl-phenyl)-acetamideYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3-chloro-4-fluorophenylamino)-N-(5-methoxy-2-methylphenyl)-acetamide (3.93 g) in anhydrous dichloromethane (450 ml) was stirred under nitrogen at −78° C. was added a solution of boron tribrouide (1M in dichloromethane, 95 ml) dropwise. The mixture was then allowed to warm to room temperature and stirred under nitrogen for 20 hours before being poured into ice/water (1 l), stirred vigorously for 1 hour and extracted into ethyl acetate (3×500 ml), dried (MgSO4) and concentrated. Purification of the residue by silica gel chromatography (eluting with 3% methanol in dichloromethane) gave the sub-title compound (2.65 g).

Workup

  1. stirringstirred vigorously for 1 hour
  2. extractionextracted into ethyl acetate (3×500 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the residue
  6. washby silica gel chromatography (eluting with 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5f8a828dd7c44504bc36c408191daae8
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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