Cesium carbonate → HCID 21106536, compound

HRID 1783678Notes

Reaction equation

HRID 1783678 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 RT. H2O (100 ml) was added and the precipitated solid was filtered and washed with EtOAc and H2O. The raw product was purified over silica gel (EtOAc:heptane 0%-60% EtOAc) 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 RT
  3. filtrationthe precipitated solid was filtered
  4. washwashed with EtOAc and H2O
  5. customThe raw product was purified over silica gel (EtOAc:heptane 0%-60% EtOAc)

Sources & evidence

ORD record
ord-d2e6c783f16f46398ced01d2a8d851dd
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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