Potassium Carbonate → 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

HRID 2357568Notes

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.[CH:13]1([NH:16][C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[C:20](B3OC(C)(C)C(C)(C)O3)[CH:19]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.ClCCl.[Pd+2].[Cl-].[Cl-].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([C:20]3[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=3[CH3:24])[C:17]([NH:16][CH:13]3[CH2:14][CH2:15]3)=[O:34])=[CH:11][CH:10]=2)[CH:5]=[N:6][N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-bromo-1-chlorophthalazine (Example 1, 0.11 g, 0.5 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.1 g, 0.5 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(ii) dichloromethane adduct (0.02 g, 0.02 mmol) in 5 mL toluene was treated with 2 M potassium carbonate (0.7 mL, 1 mmol). The mixture was stirred at 90° C. and followed by MS (product M+1=338) for 15 h. The mixture was cooled down to room temperature and purified directly via flash chromatography (silica gel) eluting with a gradient of 1/1 hexanes/EtOAc to 6% 2M ammonia in MeOH/DCM to give the title compound (0.12 g) as a yellow solid. Found MS (ES+): 338(M+H)+.

Workup

temperatureThe mixture was cooled down to room temperature
custompurified directly via flash chromatography (silica gel)
washeluting with a gradient of 1/1 hexanes/EtOAc to 6% 2M ammonia in MeOH/DCM

Sources & evidence

ORD record: ord-55a496729d134efb8aef89b45510b465
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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