Potassium Carbonate → HCID 178476278, compound

HRID 870688Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[NH:16]1[CH:20]=[C:19](B(O)O)[CH:18]=[N:17]1.[C:24](=[O:27])([O-])[O-:25].[K+].[K+]>CC#N.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:24]([OH:25])(=[O:27])[CH3:2].[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:20]3[CH:19]=[CH:18][NH:17][N:16]=3)=[CH:3][N:4]=2)[N:7]=1)[CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 3-bromo-6-(butylamino)imidazo[1,2-b]pyridazine (100 mg, 0.38 mmol), (1H-pyrazol-4-yl)boronic acid (45 mg, 0.38 mmol), PdCl2(PPh3)2 (10 mg, 0.014 mmol) and potassium carbonate (98 mg, 0.71 mmol) was dissolved in CH3CN (3 mL) and water (1.5 mL). The reaction was heated at 140° C. for 30 min in the microwave. The catalyst was filtered off celite, then the filtrate was concentrated and purified by Prep HPLC (neutral) to give N-butyl-3-(1H-pyrazol-3-yl)imidazo[1,2-b]pyridazin-6-amine acetate salt as yellow solid (1.7 mg, 2% yield): 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.12 (s, 1H), 7.86-7.92 (m, 2H), 7.30 (d, J=2.53 Hz, 1H), 7.17 (d, J=9.85 Hz, 1H), 3.47 (t, J=7.20 Hz, 2H), 1.75 (quin, J=7.26 Hz, 2H), 1.52 (sxt, J=7.43 Hz, 2H), 1.02 (t, J=7.33 Hz, 3H); LRMS (ESI) m/e 257.2 [(M+H)+, calcd for C13H17N6 257.3].

Workup

filtrationThe catalyst was filtered off celite
concentrationthe filtrate was concentrated
custompurified by Prep HPLC (neutral)

Sources & evidence

ORD record: ord-c899631f48b1483e9a9ca030076a2589
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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