Cesium carbonate → Pyridazine,3-[[2-(6-fluoro-2-pyridinyl)-1h-imidazol-1-yl]methyl]-4-propyl-6-(3-pyridinyl)-

HRID 1244265Notes

Reaction equation

HRID 1244265 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)=[C:4]([CH2:21][CH2:22][CH3:23])[CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[CH:25]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:20][C:16]1[N:15]=[C:14]([C:10]2[N:9]([CH2:8][C:5]3[N:6]=[N:7][C:2]([C:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=4)=[CH:3][C:4]=3[CH2:21][CH2:22][CH3:23])[CH:13]=[CH:12][N:11]=2)[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27343783-Pyridinylboronic acidHCID 10382055HCID 10382055, compound

Product 1

HCID 10044938Pyridazine,3-[[2-(6-fluoro-2-pyridinyl)-1h-imidazol-1-yl]methyl]-4-propyl-6-(3-pyridinyl)-

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-3-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-pyridazine (268 mg, 0.81 mmol), 3-pyridyl boronic acid (1.84 mmol), Pd2(dba)3 (37 mg, 0.04 mmol), (t-Bu)3P (8 mg, 0.04 mmol) and Cs2CO3 (600 mg, 1.84 mmol) in dioxane (6 mL) is degassed. The mixture is then heated at 100° C. for 6 hours. The solvent is removed in vacuo and water (10 mL) and EtOAc (15 mL) are added. The layers are separated and the aqueous layer is extracted with EtOAc (15 mL). The combined extracts are washed with brine (20 mL), dried (Na2SO4), and evaporated. Preparative TLC purification of the residue provides the title product.

Workup

  1. customis degassed
  2. customThe solvent is removed in vacuo and water (10 mL) and EtOAc (15 mL)
  3. additionare added
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with EtOAc (15 mL)
  6. washThe combined extracts are washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customPreparative TLC purification of the residue

Sources & evidence

ORD record
ord-4ffd6cfd447f481a84543896ae4a5a49
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

Loading…