Isobutanol → Methyl 2-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridine-5-carboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=CC(C(O)=O)=C[N:12]=1)[CH2:9][CH3:10].[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:44]([OH:48])[CH:45]([CH3:47])[CH3:46].C1C[O:52][CH2:51]C1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][CH:23]([CH3:24])[CH3:25])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:47][C:45]([C:44]([O:52][CH3:51])=[O:48])=[CH:46][N:12]=1)[CH2:9][CH3:10]Participants
Procedure
A solution of the methyl-2-[N-(5-bromo-2-(hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylate (reference example 1, paragraph 7) (0.5 g, 1.37 mmol) in THF (15 ml) was treated with triphenylphosphine (0.39 g, 1.49 mmol) and diazoethyldicarboxylate. The reaction was stirred at ambient temperature for five minutes and then isobutyl alcohol (0.152, 2.06 mmol) added. The reaction was then stirred at ambient temperature for 18 hours, partitioned between ethyl acetate and water and the aqueous layer washed with ethyl acetate (×2). The organic layers were combined, washed with water and brine, dried (MgSO4) and evaporated. The residue was subjected to chromatography (eluant: ethyl acetate/hexane) to give the title compound (0.35 g, 60%) as an off-white solid.
Workup
- stirringThe reaction was then stirred at ambient temperature for 18 hours
- custompartitioned between ethyl acetate and water
- washthe aqueous layer washed with ethyl acetate (×2)
- washwashed with water and brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-92e0cc586fe04775a94a2922b1378726
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365603B1
Reaction notes
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