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

HRID 1710783노트

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HRID 1710783 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-50c528fdb73b498db69f5842650151e0
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790720B2

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