Cesium carbonate → HCID 66742887, compound

HRID 1431045Notes

Reaction equation

HRID 1431045 reaction equation
[CH3:1][O:2][CH:3]1[CH2:6][N:5]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH2:4]1.Br[C:16]1[C:17](=[O:24])[N:18]([CH3:23])[N:19]=[C:20]([Cl:22])[CH:21]=1.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.C(=O)([O-])[O-].[Cs+].[Cs+]>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]>[Cl:22][C:20]1[CH:21]=[C:16]([NH:14][C:11]2[CH:10]=[CH:9][C:8]([CH2:7][N:5]3[CH2:6][CH:3]([O:2][CH3:1])[CH2:4]3)=[CH:13][N:12]=2)[C:17](=[O:24])[N:18]([CH3:23])[N:19]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-oneHCID 66742859HCID 66742859, compound

Product 1

HCID 66742887HCID 66742887, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
90 °C

Procedure

5-(3-Methoxy-azetidin-1-ylmethyl)-pyridin-2-ylamine (130 mg, 0.67 mmol, Eq: 1.0), 4-bromo-6-chloro-2-methyl-2H-pyridazin-3-one (165 mg, 223 mmol, Eq: 1.1), xantphos (58 mg, 0.1 mmol, Eq: 0.15), tris(dibenzylideneacetone)dipalladium(0) (46 mg, 0.05 mmol, Eq: 0.075) and cesium carbonate (767 mg, 2.35 mmol, Eq: 3.5) were added to a microwave vial. The vial was capped and purged with argon. Degassed dioxane (4.5 ml) was added to the vial through the septum and the vial was purged again, then backfilled with argon. The reaction was heated at 90° C. overnight in a sand bath. The crude reaction mixture was filtered through celite and purified by chromatography using a gradient of 5% to 25% methanol in DCM with a little added ammonium hydroxide to give 150 mg of product (63.7%).

Workup

  1. customThe vial was capped
  2. custompurged with argon
  3. additionDegassed dioxane (4.5 ml) was added to the vial through the septum
  4. customthe vial was purged again
  5. customThe crude reaction mixture
  6. filtrationwas filtered through celite
  7. custompurified by chromatography
  8. additiona little added ammonium hydroxide

Sources & evidence

ORD record
ord-cd9635fb96f84acb93331e64bdfe353f
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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