Water → HCID 59726015, compound

HRID 422547Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[N:7][N:6]=[CH:5]2.[CH3:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([NH:20][C:21]2[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=2)=[O:19])=[CH:16][C:15]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([C:15]3[CH:16]=[C:17]([CH:27]=[CH:28][C:14]=3[CH3:13])[C:18]([NH:20][C:21]3[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=3)=[O:19])=[CH:11][CH:10]=2)[CH:5]=[N:6][N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 150 mL round-bottomed flask was added 6-bromo-1-chlorophthalazine (18, 357 mg, 1465 μmol), tetrakis(triphenylphosphine)palladium (84.7 mg, 73.3 μmol), 4-methyl-N-(1-methyl-1H-pyrazol-5-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (500 mg, 1465 μmol), sodium carbonate (466 mg, 4396 μmol). The reagents were dissolved in DME:water mixture (15 mL, 4:1). The reaction mixture was stirred at 80° C. for 16 hours. The reaction mixture was evaporated and residue dissolved in ethyl acetate (20 mL) and washed with water (2×20 mL) and dried over MgSO4 and rotovaped to yield the title compound 24 as a crude product. The crude product 24 was adsorbed on silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 65% to 80% EtOAc in DCM, to provide 3-(1-chlorophthalazin-6-yl)-4-methyl-N-(1-methyl-1H-pyrazol-5-yl)benzamide (24).

Workup

customThe reaction mixture was evaporated
dissolutionresidue dissolved in ethyl acetate (20 mL)
washwashed with water (2×20 mL)
dry with materialdried over MgSO4

Sources & evidence

ORD record: ord-89745905353a46928f69daca7a2cebd4
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101612B2

Reaction notes

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