Benzyl Bromide → Methyl 1-benzyl-4-formyl-5-iodo-1H-pyrrole-2-carboxylate

HRID 1952522ノート

反応式

HRID 1952522 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[NH:6][C:7]=1[I:8])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([N:6]1[C:7]([I:8])=[C:3]([CH:1]=[O:2])[CH:4]=[C:5]1[C:9]([O:11][CH3:12])=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86664848Methyl 4-formyl-5-iodo-1H-pyrrole-2-carboxylate

生成物 1

HCID 86664847Methyl 1-benzyl-4-formyl-5-iodo-1H-pyrrole-2-carboxylate収率 90%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred solution of 4 (0.72 g, 2.6 mmol) in acetone (20 mL) was added K2CO3 (0.71 g, 5.1 mmol). The resulting mixture was stirred for 30 minutes at room temperature. Benzyl bromide (0.46 mL, 3.8 mmol) was added dropwise to the reaction mixture and the resulting mixture was refluxed for 16 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between ethyl acetate and water. The combined organic layer was dried over anhydrous MgSO4, filtered and then concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 5 as a white solid (0.85 g, 90%). 1H NMR (400 MHz, CDCl3) δ 9.66 (s, 1H), 7.50 (s, 1H), 7.24-7.25 (m, 3H), 6.98 (d, J=7.6 Hz, 2H), 5.75 (s, 2H), and 3.72 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 186.98, 160.33, 136.43, 128.97, 128.22, 127.84, 127.10, 126.59, 119.32, 92.81, 52.81, and 52.11.

後処理

  1. temperaturethe resulting mixture was refluxed for 16 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customMPLC purification (Hexanes:EtOAc/80:20) of the residue

出典と根拠

ORDレコード
ord-3d24c6dca3bd49a4880d0c1bf4672a3f
出典データセット
uspto-grants-2013_03
特許番号
US08404728B2

反応ノート

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