Potassium Carbonate → HCID 86696334, compound

HRID 870640Notes

Reaction equation

HRID 870640 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.Cl.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=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>[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343114-Aminomethylphenylboronic acid hydrochlorideHCID 86696333HCID 86696333, compound

Product 1

HCID 86696334HCID 86696334, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-(3-phenyl-propyl)-amine (100 mg, 0.3 mmol), (4-aminomethylphenyl)boronic acid hydrochloride (67 mg, 0.36 mmol), K2CO3 (124 mg, 0.9 mmol) and dichlorobis(triphenylphosphine)palladium(II) (11 mg, 0.015 mmol) in MeCN/water (3.6 ml/0.9 ml) was heated in a microwave at 150° C. for 20 min. The reaction mixture was diluted with MeOH (2 ml) and filtered. The filtrate was subjected to preparative HPLC to give the titled compound as AcOH salt (29.9 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.93 (s, 3H) 1.99-2.09 (m, 2H) 2.70-2.80 (m, 2H) 3.41 (t, J=6.95 Hz, 2H) 4.14 (s, 2H) 6.74 (d, J=9.60 Hz, 1H) 7.15-7.29 (m, 5H) 7.53 (d, J=8.34 Hz, 2H) 7.64 (d, J=9.60 Hz, 1H) 7.80 (s, 1H) 8.24 (d, J=8.59 Hz, 2H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-33b948aed1c649b1b706f8ed39dc7708
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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