Acetic Acid → HCID 59717871, compound

HRID 2197619Notes

Reaction equation

HRID 2197619 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH2:17]([NH2:22])[CH2:18][CH:19]([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][NH:22][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7894IsoamylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59717850HCID 59717850, compound

Product 1

HCID 59717871HCID 59717871, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-8e35d0489ca240bc9a2c5df571327f2e
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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