Sodium hydride → 2,6-Dichloro-4-pyrrolidino-pyridine

HRID 1437741노트

반응식

HRID 1437741 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:14]=[C:13](Cl)[CH:12]=[C:11]([Cl:16])[N:10]=1>CS(C)=O>[Cl:8][C:9]1[CH:14]=[C:13]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:12]=[C:11]([Cl:16])[N:10]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27665Pyridine, 2,4,6-trichloro-HCID 31268Pyrrolidine

생성물 1

HCID 116442082,6-Dichloro-4-pyrrolidino-pyridine수율 75%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
0 °C

실험 절차

A mixture of pyrrolidine (0.910 g, 10.7 mmol) in dry DMSO and NaH (0.385 g, 16.0 mmol) was stirred for 30 minutes at 0° C., after which a sample of 2,4,6-trichloropyridine (1.75 g, 9.63 mmol) was added. This reaction mixture was stirred at room temperature for 4 hours, after which time ice cold water was added to quench the reaction. The reaction mixture was then extracted with ethyl acetate, and the extract was washed 3-4 times with water. The organic layer was dried over sodium sulphate and concentrated. The residue was purified by column chromatography over 100-200 mesh silica gel. Elution of the column with 20% acetone in hexanes gave the pure product as a colorless solid (yield: 75%).

후처리

  1. stirringThis reaction mixture was stirred at room temperature for 4 hours
  2. additionafter which time ice cold water was added
  3. customto quench
  4. customthe reaction
  5. extractionThe reaction mixture was then extracted with ethyl acetate
  6. washthe extract was washed 3-4 times with water
  7. dry with materialThe organic layer was dried over sodium sulphate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography over 100-200 mesh silica gel
  10. washElution of the column with 20% acetone in hexanes

출처 및 근거

ORD 기록
ord-21bcc59dd55e4793b2cc91c38cd506ab
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622486B2

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