Water → 5-[4-(5-Fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid diethylamide

HRID 2055003Notes

Reaction equation

HRID 2055003 reaction equation
[CH2:1]([N:3]([CH2:37][CH3:38])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:16][CH2:17][C:18]([OH:36])([C:32]([F:35])([F:34])[F:33])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30]C)([CH3:22])[CH3:21])[N:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br.O>ClCCl>[CH2:37]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:16][CH2:17][C:18]([OH:36])([C:32]([F:34])([F:33])[F:35])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[OH:30])([CH3:21])[CH3:22])[N:7]=1)=[O:5])[CH3:38]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 207862335-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid diethylamide

Product 1

HCID 207862325-[4-(5-Fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid diethylamideYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

210 mg (0.39 mmol) of 5-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid diethylamide is mixed with 7.8 ml (7.8 mmol) of a 1 M boron tribromide solution in dichloromethane. After 20 hours at room temperature, the reaction is halted by adding water. It is extracted with ethyl acetate, the combined organic phases are washed with saturated sodium bicarbonate solution, and it is dried on sodium sulfate. After the solvent is removed and after purification on silica gel with hexane-ethyl acetate (0-100%), 56 mg (28%) of the product is obtained.

Workup

  1. extractionIt is extracted with ethyl acetate
  2. washthe combined organic phases are washed with saturated sodium bicarbonate solution, and it
  3. customis dried on sodium sulfate
  4. customAfter the solvent is removed
  5. customafter purification on silica gel with hexane-ethyl acetate (0-100%)

Sources & evidence

ORD record
ord-eee4664b324a40fa8d922c5eba00a649
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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