Dichloromethane → HCID 86689265, compound

HRID 1409526Notes

Reaction equation

HRID 1409526 reaction equation
[NH2:1][C:2]1([C:18]2[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][N:19]=2)[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:2]3([C:18]4[N:19]=[CH:20][CH:21]=[CH:22][C:23]=4[O:24][C:31]([NH2:30])=[N:1]3)[C:15]3[CH:14]=[C:13]([Cl:16])[N:12]=[CH:11][C:10]=3[O:9][C:8]2=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 517044Potassium AcetateHCID 86689264HCID 86689264, compound

Product 1

HCID 86689265HCID 86689265, 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)pyridin-3-ol (0.40 g, 1.00 mmol) in MeOH 5 mL was added potassium acetate (0.13 mL, 1.99 mmol) followed by the dropwise addition of cyanogen bromide, 3.0M solution in DCM (0.40 mL, 1.20 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was concentrated, washed with saturated NaHCO3, extracted with DCM, dried over sodium sulfate 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 DCM and washed with sat NaHCO3, brine, dried over sodium sulfate, filtered, concentrated, and purified by column chromatography on silica gel using 0-100% EtOAc/hexanes to give 0.18 g of desired product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with saturated NaHCO3
  3. extractionextracted with DCM
  4. dry with materialdried over sodium sulfate
  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 DCM
  11. washwashed
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. custompurified by column chromatography on silica gel using 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-2807abcde0964c60ab9862d2daebac64
Source dataset
uspto-grants-2014_12
Patent number
US08921363B2

Reaction notes

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