Potassium Carbonate → N-cyclopropyl-4-methyl-3-(1-(2-methylphenyl)phthalazin-6-yl)benzamide

HRID 2357532Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.Cl[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.[C:35](=O)([O-])[O-].[K+].[K+]>COCCOC.C(O)C.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:18]1([NH:17][C:15](=[O:16])[C:14]2[CH:21]=[CH:22][C:23]([CH3:24])=[C:12]([C:8]3[CH:7]=[C:6]4[C:11](=[CH:10][CH:9]=3)[C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:35])=[N:3][N:4]=[CH:5]4)[CH:13]=2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (63 mg, 212 μmol) (obtained by method C below), 2-chlorophenylboronic acid (40 mg, 254 μmol) and tetrakis(triphenylphosphine)palladium (12 mg, 11 μmol) in DME/ethanol (4:1) (5 mL) was treated with 2 M aq. potassium carbonate (317 μl, 635 μmol). The mixture was warmed to 85° C. and stirred for 3 h. The mixture was cooled to RT and purified by flash chromatography (silica gel) eluting with 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia MeOH/DCM to give N-cyclopropyl-4-methyl-3-(1-o-tolylphthalazin-6-yl)benzamide. MS (ES+): 394 (M+H)+.

Workup

temperatureThe mixture was cooled to RT
custompurified by flash chromatography (silica gel)
washeluting with 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia MeOH/DCM

Sources & evidence

ORD record: ord-6d8d9480291d400ab662f927461a49f3
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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