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

HRID 840302ノート

反応式

HRID 840302 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-92e0cc586fe04775a94a2922b1378726
出典データセット
uspto-grants-2002_04
特許番号
US06365603B1

反応ノート

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