N-bromobutanimide → N-[3-bromo-7-[3-[(methylamino)carbonyl]phenyl]imidazo[1,2-b]pyridazin-2-yl]carbamic acid methyl ester

HRID 1097310Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[NH:4][C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:22])[NH:20][CH3:21])[CH:14]=3)[CH:10]=[N:9][N:8]2[CH:23]=1.C1C(=O)N([Br:32])C(=O)C1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:24])[NH:4][C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:22])[NH:20][CH3:21])[CH:14]=3)[CH:10]=[N:9][N:8]2[C:23]=1[Br:32]

Participants

Conditions

Temperature: 0 °C

Procedure

[7-(3-Methylcarbamoyl-phenyl)-imidazo-[1,2-b]-pyridazin-2-yl]-carbamic acid methyl ester (1 eq, 0.167 mmol, 55 mg) is dissolved in DMF (1 ml) at 0° C. and NBS (1.1 eq, 0.184 mmol, 33.8 mg) is added. The reaction mixture is stirred for 1 h at 0° C. and then is diluted with EtOAc. The reaction is washed with NaHCO3 and brine, dried over MgSO4, filtered and evaporated to yield [3-Bromo-7-(3-Methylcarbamoyl-phenyl)-imidazo-[1,2-b]-pyridazin-2-yl]-carbamic acid methyl ester as a brown solid which did not require further purification; [M+H]+=406

Workup

washThe reaction is washed with NaHCO3 and brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-1150ae6119f846609dad74d2f430de88
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143253B2

Reaction notes

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