4-Hydroxybenzaldehyde → HCID 59717850, compound

HRID 2197618Notes

Reaction equation

HRID 2197618 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1>CC(N(C)C)=O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 693532,5-Dibromopyridine

Product 1

HCID 59717850HCID 59717850, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

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, acetic 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-fdd13c9eb10740b3b943d0d1084092f4
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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