Tetrahydrofuran → HCID 178515146, compound

HRID 222267Notes

Reaction equation

HRID 222267 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.C1C[O:24]CC1>O.C(O)(=O)C.OO.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([OH:24])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 2

HCID 8028TetrahydrofuranHCID 67364710(3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)boronic acid

Product 1

HCID 178515146HCID 178515146, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 784Hydrogen PeroxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)boronic acid (1.00 g, 3.5 mmol) was dissolved in a 0° C. solution of 25 mL of THF, 25 mL of water, 0.5 mL of acetic acid and 0.5 mL of 30% (w/w) hydrogen peroxide. The solution was stirred and allowed to warm to ambient temperature. After 6 h, the reaction mixture was partially concentrated and dissolved in 500 mL ethyl acetate. The organic layer was washed with water (2×100 mL), dried with magnesium sulfate, filtered, and concentrated to afford solids. The solids were dissolved in 20 mL dichloromethane and 60 mL hexanes and stirred as solids crystallized from the solution. After 2 hours, the crystalline solids were filtered and dried to afford the title compound. 1H NMR (600 MHz, DMSO-D6) δ 10.50 (s, 1H); 8.93 (s, 1H); 8.45 (s, 1H); 7.68 (d, 1H); 7.58 (d, 1H); 7.39 (d, 1H); 7.23 (d, 1H); 7.12 (d, 1H). LRMS (APCI) calculated for C14H9ClNO2 [M+H]+, 258.0; found 258.1.

Workup

  1. concentrationthe reaction mixture was partially concentrated
  2. dissolutiondissolved in 500 mL ethyl acetate
  3. washThe organic layer was washed with water (2×100 mL)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford solids
  8. customcrystallized from the solution
  9. waitAfter 2 hours
  10. filtrationthe crystalline solids were filtered
  11. customdried

Sources & evidence

ORD record
ord-62c8398e57ef411fb3cc49f4684102df
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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