Cesium carbonate → HCID 66742930, compound

HRID 1431189Notes

Reaction equation

HRID 1431189 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:11][C:12]1[N:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]2)=[CH:14][CH:13]=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+]>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]>[C:24]([N:21]1[CH2:20][CH2:19][CH:18]([C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:2]3[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[C:6]([Cl:8])[CH:7]=3)=[N:17][CH:16]=2)[CH2:23][CH2:22]1)(=[O:26])[CH3:25]

Participants

7

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 66742249HCID 66742249, compound

Product 1

HCID 66742930HCID 66742930, compoundYield 22.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

A solution of 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (201 mg, 901 μmol), 1-(4-(6-aminopyridin-3-yl)piperidin-1-yl)ethanone (180 mg, 819 μmol), Xantphos (35.5 mg, 61.4 μmol) and cesium carbonate (801 mg, 2.46 mmol) in dry dioxane (6 ml) was vacuum de-gassed and place under argon atmosphere. To this mixture was added tris(dibenzylideneacetone)dipalladium (0) (8.48 mg, 8.19 μmol) and the vacuum de-gas cycle was repeated. The material was heated at 90° C. (oil bath) with vigorous stirring overnight. The flask was cooled to ambient and the contents were filtered through a plug of celite, rinsing well with dioxane. The combined filtrate and washes were concentrated and the resulting residue was triturated with 1:1 ratio of ether/ethyl acetate. This provided the desired product as a off-white powder (66 mg, 22%). (M+H)+=362, 364 m/e

Workup

  1. customde-gassed
  2. customthe vacuum de-gas cycle
  3. temperatureThe flask was cooled to ambient and the contents
  4. filtrationwere filtered through a plug of celite
  5. washrinsing well with dioxane
  6. concentrationThe combined filtrate and washes were concentrated
  7. customthe resulting residue was triturated with 1:1 ratio of ether/ethyl acetate

Sources & evidence

ORD record
ord-53a9bebc35384371928f3eacdc08789c
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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