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

HRID 2357563Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[N:7][N:6]=[CH:5]2.[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.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>[CH:13]1([NH:12][C:8]2[C:9]3[C:4](=[CH:3][C:2]([C:26]4[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=4[CH3:30])[C:23]([NH:22][CH:19]4[CH2:20][CH2:21]4)=[O:40])=[CH:11][CH:10]=3)[CH:5]=[N:6][N:7]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of 6-bromo-N-cyclohexylphthalazin-1-amine (0.2 g, 0.65 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.2 g, 0.65 mmol), tetrakis(triphenylphosphine)palladium (38 mg, 0.0325 mmol) and 2M potassium carbonate (1 mL, 1.95 mmol) in 5 mL DME/EtOH (4:1) was stirred at 90° C. for 2 h. (Product MS found to be M+1=401). The mixture was transferred directly to a column and purified via flash chromatography (silica gel) eluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 10% 2 M ammonia in MeOH/DCM to give the title compound (0.17 g) as a yellow solid. Found MS (ES+): 401(M+H)+.

Workup

custompurified via flash chromatography (silica gel)
washeluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 10% 2 M ammonia in MeOH/DCM

Sources & evidence

ORD record: ord-6829476a1e49463b9eaa91db9f2fa710
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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