Ethyl formate → 2,6-Dichloro-4-(pyrrolidine-1-carbonyl)-pyridine-3-carbaldehyde

HRID 251635

반응식

HRID 251635 반응식
[N:1]1([CH:6]=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([Cl:18])[N:17]=1)C(O)=O.[Li+].CC([N-]C(C)C)C.[CH:27](OCC)=[O:28]>C1COCC1>[Cl:18][C:16]1[C:15]([CH:27]=[O:28])=[C:11]([C:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:7])[CH:10]=[C:9]([Cl:8])[N:17]=1

참가 물질

6

반응물 4

HCID 8025Ethyl formateHCID 773721-PyrrolidinecarboxaldehydeHCID 948302,6-Dichloroisonicotinic acidHCID 2724682Lithium diisopropylamide

생성물 1

HCID 865939852,6-Dichloro-4-(pyrrolidine-1-carbonyl)-pyridine-3-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 2,6-dichloro-pyridin-4-yl)-pyrrolidin-1-yl-methanone (2.0 g, 8.2 mmol, prepared from commercially available 2,6-dichloro-isonicotinic acid) in THF (50 mL) is added slowly LDA (4 mL, 2M in heptane/THF/ethylbenzene), maintaining an internal temperature below −65° C. The solution is stirred at −78° C. for 1 hour, then treated dropwise ethyl formate (640 mg, 8.6 mmol), again maintaining an internal temperature below −65° C. The resulting mixture is gradually warmed to room temperature and stirred overnight. The mixture is quenched with saturated NH4Cl, extracted with ether and the combined extracts are washed with brine, dried over sodium sulfate and concentrated to give crude 2,6-dichloro-4-(pyrrolidine-1-carbonyl)-pyridine-3-carbaldehyde, which is used directly for the next step.

후처리

  1. temperaturemaintaining an internal temperature below −65° C
  2. temperatureagain maintaining an internal temperature below −65° C
  3. temperatureThe resulting mixture is gradually warmed to room temperature
  4. stirringstirred overnight
  5. customThe mixture is quenched with saturated NH4Cl
  6. extractionextracted with ether
  7. washthe combined extracts are washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ab08aba5d4564124a395abc09f3f602e
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863454B2

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