Potassium Carbonate → HCID 68454136, compound

HRID 2357580Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([NH2:20])=[O:19])[CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH:21]1([NH:24][C:25](=[O:42])[C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:27]=2)[CH2:23][CH2:22]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:21]1([NH:24][C:25]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([N:12]3[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([NH2:20])=[O:19])[CH2:13]3)=[N:7][N:6]=[CH:5]4)[CH:27]=2)=[O:42])[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-(6-bromophthalazin-1-yl)piperidine-3-carboxamide (0.12g, 0.4 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide (0.1 g, 0.4 mmol), and tetrakis(triphenylphosphine)palladium (0.02 g, 0.02 mmol) in 5 mL DME/EtOH (4:1) was treated with 2 M potassium carbonate (0.5 mL, 1 mmol). The mixture resulted was warmed up to 90° C. and stirred for 1 h under nitrogen. The mixture was cooled down to room temperature, and the crude product was purified via flash chromatography (silica gel) eluting with a gradient of 4% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM to give (0.11 g) title compound as a pale yellow solid. Found MS (ES+): 430(M+H)+.

Workup

customThe mixture resulted
temperatureThe mixture was cooled down to room temperature
customthe crude product was purified via flash chromatography (silica gel)
washeluting with a gradient of 4% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM

Sources & evidence

ORD record: ord-0552be66a462444da94ef57a6a027e82
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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