Cesium carbonate → HCID 66742927, compound

HRID 1431133Notes

Reaction equation

HRID 1431133 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[N:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.Br[C:15]1[C:16](=[O:23])[N:17]([CH3:22])[N:18]=[C:19]([Cl:21])[CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>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.[Pd]>[Cl:21][C:19]1[CH:20]=[C:15]([NH:12][C:9]2[CH:8]=[N:7][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:13])[CH3:1])=[CH:11][N:10]=2)[C:16](=[O:23])[N:17]([CH3:22])[N:18]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58328452HCID 58328452, compoundHCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 66742927HCID 66742927, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

In a 15 mL microwave reaction vial was added a solution of 5-(2-(dimethylamino)ethoxy)pyrazin-2-amine (190 mg, 1.04 mmol, Eq: 1.00) in dioxane (7 ml) under argon. 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (303 mg, 1.36 mmol, Eq: 1.3), Cs2CO3 (1.02 g, 3.13 mmol, Eq: 3), xantphos (90.5 mg, 156 μmol, Eq: 0.15) and bis(dibenzylideneacetone)palladium (45.0 mg, 78.2 μmol, Eq: 0.075) were added and the reaction tube was heated in an oil bath at 105° C. (bath temp) for 7 hrs followed by stirring at room temperature overnight. The reaction mixture was filtered and the solid was washed with dioxane (20 mL) and DCM (5 mL). The combined filtrate and washes was concentrated. The residue was purified by LC chromatography eluting with 0-10% (10% NH4OH in MeOH) in (1/1) EtOAc/heptane to afford 339 mg (67%) of the title compound.

Workup

  1. customIn a 15 mL microwave reaction
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was washed with dioxane (20 mL) and DCM (5 mL)
  4. concentrationThe combined filtrate and washes was concentrated
  5. customThe residue was purified by LC chromatography
  6. washeluting with 0-10% (10% NH4OH in MeOH) in (1/1) EtOAc/heptane

Sources & evidence

ORD record
ord-163973e538354076ad7a89e0f0a37711
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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