Potassium Carbonate → (3-Cyclopent-1-enyl-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine

HRID 870722Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH3:22])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:23]1(B2OC(C)(C)C(C)(C)O2)[CH2:27][CH2:26][CH2:25][CH:24]=1.C([O-])([O-])=O.[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:23]1([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[O:20][CH2:21][CH3:22])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine (90 mg, 0.25 mmol), 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (97 mg, 0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and dichlorobis(triphenylphosphine)palladium(II) (8.8 mg, 0.013 mmol) in MeCN/water (2.8 ml/0.7 ml) was heated in a microwave at 150° C. for 15 min. The water layer was removed and the organic layer was concentrated. The residue was subjected to ISCO. The product was further purified by preparative to give the titled compound (60 mg).

Workup

customThe water layer was removed
concentrationthe organic layer was concentrated
customThe product was further purified by preparative

Sources & evidence

ORD record: ord-43d1c7a61666407986cd97d54bbe0031
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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