Cesium carbonate → 6-Bromo-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one

HRID 1783706Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[C:5](=[O:13])[N:4]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[N:3]=1.[C:24]([N:28]1[C:32]([NH2:33])=[CH:31][C:30]([CH3:34])=[N:29]1)([CH3:27])([CH3:26])[CH3:25].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>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]>[Br:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:13])[N:4]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:22])([CH3:23])[CH3:21])=[CH:16][CH:15]=1)[N:3]=[C:2]2[NH:33][C:32]1[N:28]([C:24]([CH3:27])([CH3:26])[CH3:25])[N:29]=[C:30]([CH3:34])[CH:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

11 mg 4,6-Dibromo-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one (preparation see ZA-1) were reacted with 39.0 mg 1-tert.-butyl-3-methyl-1H-pyrazol-5-ylamine, 132 mg cesium carbonate, 7.0 mg tris-(dibenzylideneacetone)-dipalladium and 8.8 mg 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were stirred under argon at 100° C. for 20 hrs until HPLC indicated complete conversion. The solvent was removed under vacuum, the residue was taken up in DCM and washed dilute HCl. Removal of the DCM and chromatography on silica in first heptane and then heptan/EtOAc 8:2 yielded 25 mg of the title product.

Workup

customThe solvent was removed under vacuum
washwashed dilute HCl
customRemoval of the DCM and chromatography on silica in first heptane

Sources & evidence

ORD record: ord-c316b6106d424f979bd720905c4400ca
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501410B2

Reaction notes

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