Isobutanol → Methyl 2-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridine-5-carboxylate

HRID 1604371Notes

Reaction equation

HRID 1604371 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH2:24][CH3:25])=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 11776TriphenylphosphineHCID 22622503methyl 2-[N-(5-bromo-2-propoxybenzyl)-N-ethylamino]pyridine-5-carboxylate

Product 1

HCID 22622491Methyl 2-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridine-5-carboxylateYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the methyl-2-[N-(5-bromo-2-(hydroxy-benzyl)-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

  1. stirringThe reaction was then stirred at ambient temperature for 18 hours
  2. custompartitioned between ethyl acetate and water
  3. washthe aqueous layer washed with ethyl acetate (×2)
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-967b209678054b8f9f725e5a74c6c7a3
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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