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

HRID 840302노트

반응식

HRID 840302 반응식
[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]

참가 물질

5

반응물 4

HCID 6560IsobutanolHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 98219072-[N-(5-Bromo-2-propoxybenzyl)-N-ethylamino]pyridine-5-carboxylic Acid

생성물 1

HCID 22622491Methyl 2-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridine-5-carboxylate수율 60%

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-92e0cc586fe04775a94a2922b1378726
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365603B1

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