Potassium Carbonate → HCID 10382055, compound

HRID 1244263Notes

Reaction equation

HRID 1244263 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8]CCl)=[C:4]([CH2:11][CH2:12][CH3:13])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)[N:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][N:25]2[CH:24]=[CH:23][N:22]=[C:21]2[C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([F:14])[N:16]=2)=[C:4]([CH2:11][CH2:12][CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 85991334HCID 85991334, compound

Product 1

HCID 10382055HCID 10382055, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DMF (30 ml) is added to a mixture of 6-chloro-3-chloroethyl-4-propyl-pyridazine (5.01 g, 24.43 mmol), 2-fluoro-6-(imidazol-2-yl)-pyridine (3.99 g, 24.43 mmol) and anhydrous K2CO3 (10.2 g, 73.3 mmol) and the mixture is stirred at room temperature overnight. The solvent is removed in vacuo, water (30 ml) and EtOAc (30 ml) are added to the residue and the layers are separated. The aqueous layer is extracted with EtOAc (3×30 ml) and the combined extracts are washed with brine (30 ml), dried (Na2SO4) and evaporated, which provides a light brown solid. The solid is washed twice with 1:1 hexane, ether (25 ml), which provides the title compound as a light yellow solid. 1H NMR (CDCl3) 8.12–8.15 (m, 1H), 7.84 (q, 1H), 7.32 (s, 1H), 7.17 (d, 1H), 7.10 (d, 1H), 6.81–6.84 (m, 1H), 6.22 (s, 2H), 2.68 (t, 2H), 1.54–1.62 (m, 2H), 0.91 (t, 3H).

Workup

  1. customThe solvent is removed in vacuo, water (30 ml) and EtOAc (30 ml)
  2. additionare added to the residue
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted with EtOAc (3×30 ml)
  5. washthe combined extracts are washed with brine (30 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customwhich provides a light brown solid
  9. washThe solid is washed twice with 1:1 hexane, ether (25 ml), which

Sources & evidence

ORD record
ord-be3c7eed18f14b65a511ce9a9174c580
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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