Chloroacetone → 1-(6-Bromimidazo[1,2-a]pyridin-3-yl)ethanone

HRID 2284625Notes

Reaction equation

HRID 2284625 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[N:8]=[CH:9]/N(C)C)=[N:6][CH:7]=1.Cl[CH2:14][C:15](=[O:17])[CH3:16].C([O-])(O)=O.[Na+]>CC(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:14]([C:15](=[O:17])[CH3:16])=[CH:9][N:8]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 178484239HCID 178484239, compound

Product 1

HCID 213456611-(6-Bromimidazo[1,2-a]pyridin-3-yl)ethanoneYield 47.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

(E)-N′-(5-Bromopyridin-2-yl)-N,N-dimethylformimidamide (2.0 g, 8.8 mmol), 1-chloropropan-2-one (1.2 mL, 1.4 g, 15 mmol), NaHCO3 (1.3 g, 15.5 mmol) in 2-propanol (30 mL) were heated at 90° C. under nitrogen for 12 h. The dark reaction mixture was cooled and the dense heterogeneous suspension was diluted with water. The solid was collected by filtration, washed with water and dried to obtain 1.0 g of 1-(6-bromoimidazo[1,2-a]pyridin-3-yl)ethan-1-one. 1H NMR (300 MHz, DMSO-d6) δ 9.62 (d, J=1.9 Hz, 1H), 8.61 (s, 1H), 7.81 (d, J=9.5 Hz, 1H), 7.75 (dd, J=9.5, 1.9 Hz, 1H), 2.55 (s, 3H). See Bioorg. Med. Chem. Lett. 15(1), 403-412 (2007); Int'l Pat. App. Pub, no. 2009/158011.

Workup

  1. customThe dark reaction mixture
  2. temperaturewas cooled
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-db303e87345348d891f2c55818a43882
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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