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

HRID 1952513노트

반응식

HRID 1952513 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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 mixture was then 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.

후처리

  1. temperaturethe mixture was then 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

출처 및 근거

ORD 기록
ord-e2bc41f0da3e4936928934ab88e38623
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404728B2

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