Potassium Carbonate → HCID 86696390, compound

HRID 870686Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.Cl.[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.CO.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>[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][O:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[O:21][CH3:22])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of ((3-bromo-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-methoxy-phenoxy)-ethyl]-amine (75 mg, 0.21 mmol), (4-aminomethylphenyl)boronic acid hydrochloride (51 mg, 0.27 mmol), K2CO3 (87 mg, 0.63 mmol) and dichlorobis(triphenylphosphine)palladium(II) (7.4 mg, 0.011 mmol) in MeCN/water (3.2 ml/0.8 ml) was heated in a microwave at 150° C. for 15 min. The reaction mixture was diluted with MeOH (3 ml) and filtered. The filtrate was subjected to preparative HPLC to give the titled compound as AcOH salt (59.6 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.93 (s, 3H) 3.76-3.83 (m, 5H) 4.13 (s, 2H) 4.26 (t, J=5.56 Hz, 2H) 6.77 (d, J=9.60 Hz, 1H) 6.85-6.99 (m, 4H) 7.51 (d, J=8.34 Hz, 2H) 7.65 (d, J=9.60 Hz, 1H) 7.79 (s, 1H) 8.21 (d, J=8.34 Hz, 2H). LRMS (ESI) m/z 390.2 [(M+H)]+, calc'd for C22H23N5O2: 389.46.

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-db8c87687cca45688bb1077b292308a5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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