Boron tribromide → HCID 86668138, compound

HRID 2370358Notes

Reaction equation

HRID 2370358 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[N:13]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=3)[C:12]2=[S:31])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9]C.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[N:13]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:28])([F:29])[F:30])[CH:20]=3)[C:12]2=[S:31])[CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86668137HCID 86668137, compound

Product 1

HCID 86668138HCID 86668138, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

The title compound was prepared according to General Method 9. A solution of 4-(3-(3-fluoro-4-(methoxymethyl)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile (80 mg, 0.177 mmol) was dissolved in DCM (3 mL) and stirred at −70° C. BBr3 (0.05 mL, 0.54 mmol) in DCM (3 mL) was added drop wise at −78° C. and the reaction mixture was allowed to warm to and stirred at RT for 2 h. The reaction mixture was poured in ice (20 g) and neutralized with saturated NaHCO3 solution, extracted with ethyl acetate (20 mL×2). The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified by silica gel chromatography to obtain 6 mg of 4-(3-(3-fluoro-4-(hydroxymethyl)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile, HPLC, Column: YMC POLYMER C18, 4.6×150 mm, 5 μm, Mobile Phase A: 0.05% TFA, Mobile Phase B: ACN, Gradient: 10% to 90% B in 15 min, hold for 3 min. 90% to 10% B in 1 min, Flow Rate: 1 mL/min, Retention time: 13.814 min, M+1, 438.

Workup

  1. customThe title compound was prepared
  2. temperatureto warm to and
  3. stirringstirred at RT for 2 h
  4. extractionextracted with ethyl acetate (20 mL×2)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-8b3dd72c9d6e432fa525b9e336367af2
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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