4-sec-Butylphenol → 3-{[4-(1-Methylpropyl)phenoxy]methyl}pyridin-2-amine

HRID 1622791

反応式

HRID 1622791 の反応式
[H-].[Na+].[CH3:3][CH:4]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH2:5][CH3:6].Cl.Cl[CH2:16][C:17]1[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][CH:22]=1>CN(C=O)C>[CH3:3][CH:4]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:16][C:17]2[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][CH:12]=1)[CH2:5][CH3:6]

参加物

5

反応物 3

HCID 74534-sec-ButylphenolHCID 24758Sodium hydrideHCID 534077753-(Chloromethyl)pyridin-2-amine hydrochloride

生成物 1

HCID 667480763-{[4-(1-Methylpropyl)phenoxy]methyl}pyridin-2-amine収率 35.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The solution of (2-aminopyridin-3-yl)methanol (1.0 g) in THF (dry) (10 mL) was added dropwise to a solution of thionyl chloride (0.736 mL) in THF (dry) (30 mL) at 0° C. The mixture was stirred at room temperature for 30 min and concentrated in vacuo to give 3-(chloromethyl)pyridin-2-amine hydrochloride as a yellow gum. NaH (60%, 147 mg) was added to a mixture of 4-(1-methylpropyl)phenol (503 mg) in DMF (dry) (7 mL) at 0° C. The mixture was stirred at the same temperature for 20 min, then was added with the prepared 3-(chloromethyl)pyridin-2-amine hydrochloride (300 mg) at the same temperature. The mixture was stirred at 0° C. for 20 min, room temperature for 1 hr and 60° C. for 1 hr. Silica-gel was added to the mixture and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (151 mg) as pale yellow crystals.

後処理

  1. stirringThe mixture was stirred at 0° C. for 20 min, room temperature for 1 hr and 60° C. for 1 hr
  2. additionSilica-gel was added to the mixture
  3. customthe volatiles were removed in vacuo
  4. customwas purified by column chromatography (silica gel, eluted with EtOAc in hexane)

出典と根拠

ORDレコード
ord-551886c62b0f45aca3b5749504889790
出典データセット
uspto-grants-2014_07
特許番号
US08778934B2

関連ノート

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