Cesium carbonate → HCID 58044170, compound

HRID 1919108Notes

Reaction equation

HRID 1919108 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=2)[CH2:14][CH2:13]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>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].O1CCOCC1>[Cl:8][C:6]1[CH:7]=[C:2]([NH:24][C:21]2[CH:20]=[CH:19][C:18]([N:15]3[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]3)=[CH:23][N:22]=2)[C:3](=[O:10])[N:4]([CH3:9])[N:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 223298335-(4-Methylpiperazin-1-yl)pyridin-2-amineHCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 58044170HCID 58044170, compoundYield 53.5%

Reagents, catalysts & solvents 2

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

Procedure

Following Example 119b, 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (1.5 g, 6.7 mmol), 5-(4-methyl-piperazin-1-yl)-pyridin-2-ylamine (1.3 g, 6.7 mmol), cesium carbonate (4.8 g, 39.4 mmol), and Xantphos (330 mg, 8.5 mol %), dioxane (50 ml) and tris(dibenzylideneacetone)dipalladium(0) (307 mg, 5 mol %) were reacted. Purified via column chromatography: ISCO 40 g silica, 50-100% ethyl acetate/hexanes then 0-10% methanol to give 307a (1.2 g, 53%) as a light tan solid.

Workup

  1. customwere reacted
  2. customPurified via column chromatography

Sources & evidence

ORD record
ord-50ca4965b5bb4bb7a53c4f579b564b2e
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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