Cesium carbonate → HCID 58540266, compound

HRID 1907805Notes

Reaction equation

HRID 1907805 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[N:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.Br[C:15]1[C:16](=[O:22])[NH:17][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>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:21][C:19]1[CH:20]=[C:15]([NH:13][C:10]2[N:11]=[N:12][C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:8][CH:9]=2)[C:16](=[O:22])[NH:17][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 115865224-Bromo-6-chloro-2,3-dihydropyridazin-3-oneHCID 45787835HCID 45787835, compound

Product 1

HCID 58540266HCID 58540266, compoundYield 41.1%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

A 25-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with 6c (170 mg, 0.98 mmol), 4-bromo-6-chloropyridazin-3(2H)-one (411 mg, 1.97 mmol), cesium carbonate (956 mg, 8.61 mmol), and 1,4-dioxane (7 mL). After bubbling nitrogen through the resulting suspension for 30 min, Xantphos (48 mg, 0.08 mmol) and tris(dibenzylideneacetone)dipalladium(0) (45 mg, 0.05 mmol) were added, and the reaction mixture was heated for 16 h in a 130° C. bath. After this time, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica to afford a 41% yield (121 mg) of 6e as an off-white solid: mp 263-265° C.; 1H NMR (300 MHz, DMSO-d6) δ 13.29 (s, 1H), 1.0.10 (s, 1H), 8.75 (dd, 2H, J=4.8, 1.8 Hz), 8.52 (s, 1H), 8.35 (d, 1H, J=9.3 Hz), 8.11 (dd, 2H, J=4.5, 1.5 Hz), 8.01 (d, 1H, J=9.3 Hz); MS (ESI+) 301.1 (M+H).

Workup

  1. customA 25-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet
  2. customAfter bubbling nitrogen through the resulting suspension for 30 min
  3. temperatureAfter this time, the mixture was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-c06e528dc9194258b3edf3a5472b1365
Source dataset
uspto-grants-2013_12
Patent number
US08598174B2

Reaction notes

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