Chloroacetaldehyde → 6-Fluoroimidazo[1,2-b]pyridazine

HRID 870618Notes

Reaction equation

HRID 870618 reaction equation
[F:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH:11]=O>C(O)CCC.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[CH:11][N:8]=2)[N:7]=1

Participants

5

Reactant 2

HCID 33ChloroacetaldehydeHCID 137190686-Fluoropyridazin-3-amine

Product 1

HCID 151444366-Fluoroimidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 3283Diethyl EtherSolvent

Procedure

6-Fluoro-pyridazin-3-ylamine [108784-42-5] (10 g, 89 mmol) was combined with a 50% (w/v) aqueous solution of chloroacetaldehyde [107-20-0] (23 mL, 177 mmol) in n-butanol (150 mL) and stirred at reflux for 1 h. The cooled reaction solution was reduced in volume and diluted with diethyl ether to precipitate a brown solid, which was collected by filtration, to yield 12.0 g. LRMS (ESI) m/z 138.0 [(M+H)]+, calc'd for C6H4FN3: 137.12.

Workup

  1. temperatureat reflux for 1 h
  2. customThe cooled reaction solution
  3. customto precipitate a brown solid, which
  4. filtrationwas collected by filtration
  5. customto yield 12.0 g

Sources & evidence

ORD record
ord-257dec75ef4a470bb20851afaca572a2
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

Loading…