N-bromobutanimide → ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1508497ノート

反応式

HRID 1508497 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:13][C:6]1[N:2]([CH3:1])[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][C:5]=1[CH3:7]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 14296950ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 67516409ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

To a solution of ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate (63 mg, 0.377 mmol) in CHCl3 (3.5 mL) at 0° C. was added N-bromosuccinimide (67.1 mg, 0.377 mmol). The reaction was stirred at 0° C. for 15 min. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate. LCMS calc.=245.0. found=245.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.83 (s, 1H); 4.27 (q, J=7.1 Hz, 2H); 3.91 (s, 3H); 2.05-2.02 (m, 3H); 1.34 (t, J=7.1 Hz, 3H).

後処理

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1))

出典と根拠

ORDレコード
ord-7fb169b1beb84f2d9e71975dec1c2979
出典データセット
uspto-grants-2015_12
特許番号
US09221834B2

反応ノート

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