Potassium Carbonate → HCID 68456030, compound

HRID 2357588Notes

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.[CH3:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:27]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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]>[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:27]3[C:28]([CH3:33])=[CH:29][C:30]([CH3:32])=[CH:31][C:26]=3[CH3:25])=[N:3][N:4]=[CH:5]4)[CH:13]=2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (0.110 g, 326 μmol), 2,4,6-trimethylbenzeneboronic acid (53 mg, 326 μmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(ii) dichloromethane adduct (12mg, 16 μmol) in 5 mL toluene/ethanol (4:1) was treated with 2 M potassium carbonate (488 μl, 977 μmol). The mixture was stirred at 100° C. under nitrogen and followed by MS for about 15 h. (product MS=422 (M+1)). The mixture was concentrated under vacuum and the crude product was purified via flash chromatography (silica gel) eluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM to give the title compound (80 mg). Found MS (ES+): 422(M+H)+.

Workup

concentrationThe mixture was concentrated under vacuum
customthe crude product was purified via flash chromatography (silica gel)
washeluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM

Sources & evidence

ORD record: ord-3b3105f7d5164ab584d9ab0c81357c34
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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