Potassium Carbonate → HCID 86728281, compound

HRID 1776896Notes

Reaction equation

HRID 1776896 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]3[C:17]=2[CH2:18][OH:19])[C:5](Cl)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]3[N:10]=[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]4[C:17]=3[CH2:18][O:19][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86728280HCID 86728280, compound

Product 1

HCID 86728281HCID 86728281, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-(5-bromo-2-chloropyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)methanol (20 mg, 0.06 mmol) in DMF (2 mL), K2CO3 (20 mg, 0.14 mmol) was stirred at 100° C. overnight. The reaction mixture was concentrated in vacuo. The resulting residue was suspended with water and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified using PTLC (eluted with dichloromethane:MeOH=50:1) to provide 2-bromo-4-aza-6H-chromeno[4′,3′:4,5]imidazo[1,2-a]pyridine (7 mg, yield: 39%). 1H-NMR (CDCl3, 400 MHz) δ 8.23 (d, J=2.4 Hz, 1H), 8.13 (d, J=2.4 Hz, 1H), 7.75 (d, J=6.8 Hz, 1H), 7.66 (d, J=9.2 Hz, 1H), 7.27˜7.30 (m, 1H), 6.90˜6.95 (m, 1H), 5.93 (s, 2H). MS (M+H)+: 302/304.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified
  8. washPTLC (eluted with dichloromethane:MeOH=50:1)

Sources & evidence

ORD record
ord-00a0c926363f45ada759bc281b97a1a9
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

Loading…