N-bromobutanimide → 3-(3-Bromo-imidazo-[1,2-b]-pyridazin-7-yl)-N-methyl-benzamide

HRID 1097321Notes

Reaction equation

HRID 1097321 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[C:7]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([NH:15][CH3:16])=[O:14])[CH:6]=[N:5]2.C1C(=O)N([Br:27])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:27][C:3]1[N:4]2[N:5]=[CH:6][C:7]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])=[CH:8][C:9]2=[N:1][CH:2]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 594435013-imidazo[1,2-b]pyridazin-7-yl-N-methylbenzamide

Product 1

HCID 444734593-(3-Bromo-imidazo-[1,2-b]-pyridazin-7-yl)-N-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Imidazo-[1,2-b]-pyridazin-7-yl-N-methyl-benzamide (1 eq, 0.595 mmol, 150 mg) is dissolved in DMF (5 ml) at 0° C. and NBS (1.1 eq, 0.654 mmol, 116 mg) is added. The reaction mixture is stirred for 1 h at 0° C. and then is diluted with EtOAc. The reaction mixture is washed with NaHCO3 and brine, dried over MgSO4, filtered and evaporated to yield 3-(3-Bromo-imidazo-[1,2-b]-pyridazin-7-yl)-N-methyl-benzamide as a pale yellow solid which did not require further purification; [M+H]+=333

Workup

  1. washThe reaction mixture is washed with NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f3a100cfaa204f1095b3c4335e86f93d
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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