Sodium Iodide → Methyl 2-{3-bromo-4-[3-(2-methyl-1-pyrrolidinyl)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylate

HRID 1710783ノート

反応式

HRID 1710783 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH3:22])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11]Cl.[CH3:23][CH:24]1[CH2:28][CH2:27][CH2:26][NH:25]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH3:22])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:25]1[CH2:26][CH2:27][CH2:28][CH:24]1[CH3:23]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457515Methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 59457482Methyl 2-{3-bromo-4-[3-(2-methyl-1-pyrrolidinyl)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylate収率 8%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

A suspension of methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i91 (0.5 g, 1.24 mmol, 1 eq), 2-methylpyrrolidine (0.3 ml, 3.0 mmol, 2.5 eq), potassium carbonate (0.68 g, 5 mmol, 4 eq) and sodium iodide (20 μg, 0.12 mmol, 0.1 eq) in acetonitrile (10 ml) is stirred overnight at 90° C. The resulting mixture is taken up with dichloromethane, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The crude product is triturated in diethyl ether to afford 50 mg of methyl 2-{3-bromo-4-[3-(2-methyl-1-pyrrolidinyl)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylate 126.

後処理

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is triturated in diethyl ether

出典と根拠

ORDレコード
ord-50c528fdb73b498db69f5842650151e0
出典データセット
uspto-grants-2010_09
特許番号
US07790720B2

反応ノート

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