Sodium Carbonate → HCID 135745012, compound

HRID 643640Notes

Reaction equation

HRID 643640 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]2=[N:7][N:8]([C:10]3[CH:15]=[CH:14][C:13]([N:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=3)[N:9]=[C:5]2[CH:4]=1.B(Br)(Br)Br.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:20]=[CH:19][C:6]2=[N:7][N:8]([C:10]3[CH:11]=[CH:12][C:13]([N:16]([CH3:17])[CH3:18])=[CH:14][CH:15]=3)[N:9]=[C:5]2[CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 24756730HCID 24756730, compound

Product 1

HCID 135745012HCID 135745012, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, 130 mg (5 mmol) of 9f was dissolved in (5 ml) CH2Cl2, at 0° C. was slowly added 0.458 ml (50 mmol) of BBr3. The solution was stirred overnight at room temperature. The reaction was poured into ice/water and alkalinized with Na2CO3 (aqueous) and the organic layer was extracted and dried over Na2SO4. After removing the solvent by evaporation, the residue was purified by chromatography (dichloromethane/ethyl acetate, 95/5). The solvent was evaporated to obtain 91 mg (74%) of 9h as yellow solid.

Workup

  1. extractionthe organic layer was extracted
  2. dry with materialdried over Na2SO4
  3. customAfter removing the solvent
  4. customby evaporation
  5. customthe residue was purified by chromatography (dichloromethane/ethyl acetate, 95/5)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-792a61aef7fd4bfab83c8e40e39fb522
Source dataset
uspto-grants-2010_04
Patent number
US07700616B2

Reaction notes

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