Water → HCID 86630869, compound

HRID 17527Notes

Reaction equation

HRID 17527 reaction equation
[C:1]([C:3]1[C:4]([O:24]C)=[C:5]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]([F:16])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]=1[CH3:9])#[N:2].O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([C:3]1[C:4]([OH:24])=[C:5]([NH:17][C:18](=[O:23])[C:19]([CH3:20])([CH3:21])[CH3:22])[C:6]([F:16])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]=1[CH3:9])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86630868N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

Product 1

HCID 86630869HCID 86630869, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide (I-237) (200 mg, 0.59 mmol) was dissolved in dichloromethane (5 ml), and under nitrogen atmosphere at −78° C., 1 M borondichloromethane tribromide solution (1.76 ml, 1.76 mmol) was dropwise added. With stirring, the solution was heated up to 0° C., taking 3 hours. At the same temperature, water with ice was gradually dropwise added to it, followed by stirring for 5 minutes. Further, an aqueous saturated sodium hydrogencarbonate solution was added to the solution to make pH=7. The solution was extracted twice with dichloromethane. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1) to obtain the entitled compound (125 mg, 65%) as a white solid.

Workup

  1. stirringby stirring for 5 minutes
  2. extractionThe solution was extracted twice with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d4fee1ca6dbe461aab1205933531c6cc
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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