N-bromobutanimide → 4-(3-bromo-imidazo[1,2-b]pyridazin-7-yl)-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one

HRID 1097315Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[C:7]([C:10]1[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:12](=[O:25])[CH:11]=1)[CH:6]=[N:5]2.[Br:26]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Br:26][C:3]1[N:4]2[N:5]=[CH:6][C:7]([C:10]3[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]4)[C:12](=[O:25])[CH:11]=3)=[CH:8][C:9]2=[N:1][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Imidazo[1,2-b]pyridazin-7-yl-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one (1 eq, 0.122 mmol, 41.3 mg) is dissolved in DMF (10 ml) and N-bromosuccinimide (1.1 eq, 0.135 mmol, 24.2 mg) is added. The reaction mixture is then stirred at 0° C. for 30 min. The reaction is diluted with EtOAc and washed with NaHCO3 and brine. The organic phase is then dried over MgSO4, filtered and evaporated to dryness to give 4-(3-bromo-imidazo[1,2-b]pyridazin-7-yl)-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one as a brown solid which did not require any further purification; [M+H]+=417

Workup

washwashed with NaHCO3 and brine
dry with materialThe organic phase is then dried over MgSO4
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-bd2a38f2da41465da83b8a4a17a3906c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143253B2

Reaction notes

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