Dichloromethane → HCID 86689262, compound

HRID 1409522Notes

Reaction equation

HRID 1409522 reaction equation
[NH2:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])[C:15]2[CH:14]=[C:13]([Cl:16])[N:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:17])=[CH:6][CH:7]=2.C([O-])(=O)C.[K+].[N:30]#[C:31]Br.C(Cl)Cl>CO>[Br:17][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][CH:6]=1)[O:9][C:10]1[CH:11]=[N:12][C:13]([Cl:16])=[CH:14][C:15]=1[C:2]12[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C:31]([NH2:30])=[N:1]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 517044Potassium AcetateHCID 86689261HCID 86689261, compound

Product 1

HCID 86689262HCID 86689262, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)phenol (0.406 g, 1.006 mmol) in MeOH 5 mL was added potassium acetate (0.126 mL, 2.012 mmol) followed by the dropwise addition of cyanogen bromide, 3.0M solution in DCM (0.402 mL, 1.207 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was concentrated, washed with sat. NaHCO3, extracted with DCM, dried over Na2SO4 and concentrated. The resulting product was dissolved in 1,2-dichloroethane followed by the addition of 4.0 M HCl in dioxane (15 mL) and stirred at RT for 1.5 h. The reaction mixture was concentrated, diluted with dichloromethane and washed with saturated NaHCO3 solution, brine, dried over Na2SO4, filtered, concentrated. The crude material was purified by chromatography on silica gel using gradient of 0-100% EtOAc/hexanes to give the desired product. MS m/z=429.8 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with sat. NaHCO3
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. dissolutionThe resulting product was dissolved in 1,2-dichloroethane
  7. additionfollowed by the addition of 4.0 M HCl in dioxane (15 mL)
  8. stirringstirred at RT for 1.5 h
  9. concentrationThe reaction mixture was concentrated
  10. additiondiluted with dichloromethane
  11. washwashed with saturated NaHCO3 solution, brine
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe crude material was purified by chromatography on silica gel using gradient of 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-3d6db2596b554a9eb2e8f66f4e0ff00f
Source dataset
uspto-grants-2014_12
Patent number
US08921363B2

Reaction notes

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