Potassium Carbonate → HCID 59717850, compound

HRID 601570Notes

Reaction equation

HRID 601570 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.[CH3:15][C:16](N(C)C)=[O:17]>>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([O:17][C:16]2[CH:13]=[CH:12][C:11]([CH:1]=[O:4])=[CH:10][CH:15]=2)=[N:9][CH:10]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 693532,5-Dibromopyridine

Product 1

HCID 59717850HCID 59717850, compound

Procedure

As shown in scheme 7,4-Hydroxybenzaldehyde is treated with potassium carbonate and 2,5-dibromopyridine in DMAC to afford 4-(5-bromo-pyridin-2-yloxy)-benzaldehyde (35). The aldehyde 35 is combined with isoamylamine, sodium triacetoxyborohydride, acectic acid, and dichloromethane to yield the reductive amination product [4-(5-bromo-pyridin-2-yloxy)-benzyl]-(3-methyl-butyl)-amine (36). The resulting aryl bromide 36 is treated with acetamide, copper iodide, and 1,2 diaminocyclohexane in dioxane to yield the target compound 37.

Sources & evidence

ORD record
ord-d3d6df9cad5f4216b99cdb029e6875ae
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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