Cesium carbonate → HCID 21106536, compound

HRID 1765362Notes

Reaction equation

HRID 1765362 reaction equation
Br[C:2]1(Br)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][CH2:14][O:15][CH3:16])[NH:3]1.[C:18]([N:22]1[C:26]([NH2:27])=[CH:25][C:24]([CH3:28])=[N:23]1)([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>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].O>[C:18]([N:22]1[C:26]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:12])[N:4]([CH2:13][CH2:14][O:15][CH3:16])[N:3]=2)=[CH:25][C:24]([CH3:28])=[N:23]1)([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7372001-tert-Butyl-3-methyl-1H-pyrazol-5-amineHCID 21106544HCID 21106544, compound

Product 1

HCID 21106536HCID 21106536, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

4-Bromo-2-(2-methoxyethyl)-4-bromo-2H-phthalazin-1-one (0.57 g, 2.0 mmol), 1-(tert-butyl)-3-methyl-1H-pyrazol-5-ylamine (0.46 g, 3.0 mmol), Cs2CO3 (0.98 mg, 3.0 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.092 g, 0.1 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.17 mg, 0.3 mmol) were dissolved in degassed dioxane (10 ml). The reaction mixture was heated with stirring to 130° C. for 8 hours and then cooled to room temperature. H2O (100 ml) was added and the precipitated solid was filtered and washed with ethyl acetate and H2O. The raw product was purified over silica gel (ethyl acetate:heptane 0%-60% ethyl acetate) to give the title compound (0.46 g, 65% yield). 1H-NMR: (400 MHz, D6-DMSO) 8.22–8.31 (3H, m), 7.95 (1H, t), 7.86 (1H, t), 5.91 (1H, s), 4.05 (1H, t), 3.55 (1H, t), 3.17 (3H, s), 2.14 (3H, s), 1.54 (9H, s); MS (ESI+)=356.3 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled to room temperature
  3. filtrationthe precipitated solid was filtered
  4. washwashed with ethyl acetate and H2O
  5. customThe raw product was purified over silica gel (ethyl acetate:heptane 0%-60% ethyl acetate)

Sources & evidence

ORD record
ord-9a3458fd216e4352ae5fc9b92af8a9c0
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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