Diisopropylethylamine → 3-Bromo-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

HRID 225521

반응식

HRID 225521 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10]Br)[C:5]([CH2:8]Br)=[N:6][CH:7]=1.[C:12]([NH2:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][N:31]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:8][C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 138598TritylamineHCID 577536665-Bromo-2,3-bis(bromomethyl)pyridine

생성물 1

HCID 577536743-Bromo-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 0.87 mmol 5-Bromo-2,3-bis-bromomethyl-pyridine, 1.1 mmol tritylamine, and 2.61 mmol DIPEA in 3 ml DMF was stirred at 60° C. for 2 h. The reaction mixture was evaporated in vacuo. The residue was taken in water and extracted with ethylacetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/dichloromethane) to yield the title compound as a light brown solid. MS (m/e): 243.4 (tritylion, 100%)

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. extractionextracted with ethylacetate
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (SiO2, heptane/dichloromethane)

출처 및 근거

ORD 기록
ord-a137a8f9ca30484f9ca5f82197ed84d8
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557114B2

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