Potassium Carbonate → HCID 10337487, compound

HRID 1244254Notes

Reaction equation

HRID 1244254 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][C:9]1[N:10]=[N:11][C:12]([O:18][CH2:19][CH3:20])=[CH:13][C:14]=1[O:15][CH2:16][CH3:17].[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[NH:29][CH:30]=[CH:31][N:32]=2)[N:23]=1>CN(C=O)C>[CH2:16]([O:15][C:14]1[CH:13]=[C:12]([O:18][CH2:19][CH3:20])[N:11]=[N:10][C:9]=1[CH2:8][N:32]1[CH:31]=[CH:30][N:29]=[C:28]1[C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([F:21])[N:23]=1)[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 21919298HCID 21919298, compound

Product 1

HCID 10337487HCID 10337487, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Excess K2CO3 is added to a stirred solution of 3-chloromethyl-4,6-diethoxy-pyridazine (70 mg, 0.32 mmol) and 2-fluoro-6-(1H-imidazol-2-yl)-pyridine (52 mg, 0.32 mmol) in DMF (6 mL). The mixture is stirred at room temperature overnight. The solvent is removed in vacuo and water (5 mL) and EtOAc (8 mL) are added. The layers are separated and the aqueous layer is extracted with EtOAc (8 mL). The combined extracts is washed with brine (10 mL) and dried (Na2SO4) and evaporated. Preparative TLC purification of the residue (5% MeOH in CH2Cl2) provides the title compound as a light yellow oil. H1 NMR δ (CDCl3) 8.07–8.10 (m, 1H), 7.82 (q, 1H, J=7.8 Hz), 7.14 (s, 2H), 6.80–6.84 (m, 1H), 6.22 (s, 1H), 6.11 (s, 2H), 4.50 (q, 2H, J=7.2 Hz), 3.95 (q, 2H, J=7.2 Hz), 1.39 (t, 3H, J=7.2 Hz), 1.18 (t, 3H, J=7.2 Hz).

Workup

  1. customThe solvent is removed in vacuo and water (5 mL) and EtOAc (8 mL)
  2. additionare added
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (8 mL)
  5. washThe combined extracts is washed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPreparative TLC purification of the residue (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ac8feb5ceab54cb28f44b4226b0cc817
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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