Sodium Bicarbonate → HCID 178510911, compound

HRID 1921263Notes

Reaction equation

HRID 1921263 reaction equation
[CH:1]1([CH2:7][CH:8]([C:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20]C)=[CH:17][CH:18]=3)[NH:13][N:12]=2)[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.C(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]1([CH2:7][CH:8]([C:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[NH:13][N:12]=2)[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 178487482HCID 178487482, compound

Product 1

HCID 178510911HCID 178510911, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-cyclohexyl-2-(6-methoxy-1H-indazol-3-yl)propanenitrile (1.61 g, 5.68 mmol) was dissolved in CH2Cl2 and cooled with an ice bath. BBr3/CH2Cl2 1M (8.6 ml, 8.52 mmol) was added to this mixture, which was stirred at 50° C., then poured onto saturated NaHCO3 solution, extracted with ethylacetate, dried over Na2SO4, filtered, concentrated under vacuum and purified by flash chromatography (CH2Cl2/MeOH 98/2). Crystallisation from EtOH gave 780 mg of white crystals (51%). mp 175° C.

Workup

  1. temperaturecooled with an ice bath
  2. extractionextracted with ethylacetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. custompurified by flash chromatography (CH2Cl2/MeOH 98/2)
  7. customCrystallisation from EtOH

Sources & evidence

ORD record
ord-6cb85c0ce6ef4f0ca0d1d3ef701b6bcc
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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