Phenol → N-(6-phenoxyimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

HRID 1668029Notes

Reaction equation

HRID 1668029 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].I[C:15]1[CH:16]=[CH:17][C:18]2[N:19]([CH:21]=[C:22]([NH:24][C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])[N:23]=2)[N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:7]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([CH:21]=[C:22]([NH:24][C:25]([CH:27]3[CH2:28][CH2:29]3)=[O:26])[N:23]=2)[N:20]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 23665647Potassium tert-butoxideHCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Product 1

HCID 57505580N-(6-phenoxyimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamideYield 54.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using phenol (69 mg, 0.73 mmol), N,N-dimethylformamide (25.0 mL), potassium tert-butoxide (1.16 g, 10.3 mmol), N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (200 mg, 0.61 mmol) and potassium carbonate (42 mg, 0.31 mmol), and in the same manner as in Example 216, the title compound (98 mg, 54%) was obtained as a white powder.

Sources & evidence

ORD record
ord-e930f37ce66e4273aff5b815ac24aef7
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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