Sodium Bicarbonate → HCID 86759956, compound

HRID 1745915Notes

Reaction equation

HRID 1745915 reaction equation
COCC[O:5][C:6]1[CH:32]=[CH:31][C:9]2[N:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[C:16]([O:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:11]=[N:12][C:8]=2[CH:7]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:5][C:6]1[CH:32]=[CH:31][C:9]2[N:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[C:16]([O:23][S:24]([C:27]([F:28])([F:29])[F:30])(=[O:25])=[O:26])[CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:11]=[N:12][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86759957HCID 86759957, compound

Product 1

HCID 86759956HCID 86759956, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoro-methanesulfonic acid 2-[5-(2-methoxy-ethoxy]benzoimidazol-1-yl]-quinolin-8-yl ester 77E (2.00 g, 4.28 mMol) was suspended in 20 mL of anydrous DCM under an atmosphere of dry N2. To this heterogeneous solution was added 12.9 mL of a solution of 1 M borontribromide in DCM and the resulting mixture was stirred at ambient temperature for 24 hours. The reaction mixture was then poured into ice water. The resulting heterogeneous mixture was neutralised with the addition of NaHCO3 and then partitioned between isopropanol/DCM (1882) and aqueous saturated NaHCO3. The organic layer was washed again aqueous saturated NaHCO3, dried over Na2SO4, filtered, concentrated under vacuum to give 890 mg of a brownish yellow solid as the title compound 116A.

Workup

  1. custompartitioned between isopropanol/DCM (1882) and aqueous saturated NaHCO3
  2. washThe organic layer was washed again aqueous saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5cb23da4f8ca49ffb8a4e0e898639304
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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