4-Bromopyridinium chloride → Pyridazine, 3-phenyl-5-(4-pyridinyl)-

HRID 130337

Reaction equation

[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([Sn](CCCC)(CCCC)CCCC)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Br[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>C1COCC1.C(Cl)Cl.[NH4+].[Cl-].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>[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

3-Phenyl-5-(tri-n-butylstannyl)pyridazine (110 mg, 0.247 mmol), 4-bromopyridine hydrochloride (72 mg, 0.370 mmol) and Pd(PPh3)4 (10 mg) in THF (2 ml) were combined and heated to 150° C. for 60 min in a Smith Synthesiser microwave reactor (Personal Chemistry, Uppsala, Sweden). The reaction was diluted with CH2Cl2 (6 ml) and NH4Cl (2 ml) then poured into PTFE (5 μM) fritted syringe barrels. The organic phase was collected and concentrated while loading onto silica. The compound was purified by dry flash column chromatography to give the title compound as a white solid (40 mg). δH (400 MHz, d6 DMSO) 7.36-7.63 (3H, m), 8.10 (2H, dd, J 1.8 and 4.5), 8.32 (2H, m), 8.62 (1H, d, J 2.0), 8.80-8.82 (2H, dd, J 1.8 and 4.5), 9.71 (2H, d, J 2.0); m/z (ES+) 234 (MH+).

Workup

additionthen poured into PTFE (5 μM) fritted syringe barrels
customThe organic phase was collected
concentrationconcentrated
customThe compound was purified
customby dry flash column chromatography

Sources & evidence

ORD record: ord-6ab7387de01244b79f01f726fa6820c7
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381725B2

Linked notes

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