Cesium carbonate → 4-(2-chloropyridin-4-yl)phthalazin-1(2H)-one

HRID 535497Notes

Reaction equation

HRID 535497 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1.[Cl:13][C:14]1[CH:19]=[C:18](B(O)O)[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:13][C:14]1[CH:19]=[C:18]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:12])[NH:4][N:3]=2)[CH:17]=[CH:16][N:15]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27751424-chlorophthalazin-1(2H)-oneHCID 51515952-Chloropyridine-4-boronic acid

Product 1

HCID 866735574-(2-chloropyridin-4-yl)phthalazin-1(2H)-one

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-chlorophthalazin-1(2H)-one (300 mg, 1.66 mmol), 2-chloropyridin-4-ylboronic acid (314 mg, 1.99 mmol), Cs2CO3 (1080 mg, 3.32 mmol) and PdCl2(dppf) (71.5 mg, 0.083 mmol) in dioxane (6 mL) was heated at 160° C. under microwave condition for 20 minutes. The mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered, and concentrated to afford the title compound: MS (APCI) M/Z 257 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3daf460ccd9c4202a4f5dc2428c52bde
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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