Sodium Carbonate → 1-(3-piperidin-1-yl-propyl)-4-[3-(3-pyrazol-1-yl-phenyl)imidazo[1,2-b]pyridazin-7-yl]-1H-pyridin-2-one

HRID 1097316Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)[C:13](=[O:26])[CH:12]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.[N:27]1([C:32]2[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=2)[CH:31]=[CH:30][CH:29]=[N:28]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[N:20]1([CH2:19][CH2:18][CH2:17][N:14]2[CH:15]=[CH:16][C:11]([C:9]3[CH:8]=[N:7][N:6]4[C:2]([C:36]5[CH:35]=[CH:34][CH:33]=[C:32]([N:27]6[CH:31]=[CH:30][CH:29]=[N:28]6)[CH:37]=5)=[CH:3][N:4]=[C:5]4[CH:10]=3)=[CH:12][C:13]2=[O:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Conditions

Temperature: 120 °C

Procedure

4-(3-Bromo-imidazo[1,2-b]pyridazin-7-yl)-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one (1.0 eq, 0.096 mmol, 40 mg), [3-(1H-pyrazol-1-yl)phenyl]boronic acid (1.50 eq, 0.144 mmol, 28.5 mg) and Na2CO3 (2.0 eq, 0.192 mmol, 20.4 mg) are dissolved in DME/H2O (3/1 ml) and PdCl2(PPh3)2 (0.1 eq, 0.0096 mmol, 6.74 mg) is added. The reaction mixture is then heated in a microwave at 120° C. for 10 min. At the completion of this time the solvent is removed in vacuo and the product is purified by flash column chromatography eluting with CH2Cl2/MeOH (80:20) to give 1-(3-piperidin-1-yl-propyl)-4-[3-(3-pyrazol-1-yl-phenyl)imidazo[1,2-b]pyridazin-7-yl]-1H-pyridin-2-one as a yellow solid; [M+H]+=480

Workup

customAt the completion of this time the solvent is removed in vacuo
customthe product is purified by flash column chromatography
washeluting with CH2Cl2/MeOH (80:20)

Sources & evidence

ORD record: ord-e6796222a78e4602b05bf22a691f3cf8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143253B2

Reaction notes

Loading…