Ethyl chloroformate → Ethyl 3,5-dibromoisonicotinate

HRID 1501277노트

반응식

HRID 1501277 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[Li+].CC([N-]C(C)C)C.[C:17](Cl)(=[O:21])[O:18][CH2:19][CH3:20]>C1COCC1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[C:7]=1[C:17]([O:18][CH2:19][CH3:20])=[O:21]

참가 물질

5

반응물 3

HCID 10928Ethyl chloroformateHCID 693693,5-DibromopyridineHCID 2724682Lithium diisopropylamide

생성물 1

HCID 46311332Ethyl 3,5-dibromoisonicotinate수율 29%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 3,5-dibromopyridine (5 g, 21.11 mmol) in THF was added LDA (2 M in THF, 12.66 ml, 25.33 mmol) at −78° C. The mixture was stirred at −78° C. for 45 min. Then ethyl carbonochloridate (2.29 g, 21.11 mmol) was added and the mixture stirred at −78° C. for 1 hours. After reaction completed, the reaction was quenched by addition of 5 mL of saturated NH4Cl and extracted with EtOAc. The extractions were combined, washed with H2O, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash column (Eluent: PE/EtOAc=10:1), to give ethyl 3,5-dibromoisonicotinate as a yellow solid. (1.9 g, yield 29%) LCMS (M+H+) m/z: calcd 306.8. found 309.7.

후처리

  1. stirringthe mixture stirred at −78° C. for 1 hours
  2. customAfter reaction
  3. customthe reaction was quenched by addition of 5 mL of saturated NH4Cl
  4. extractionextracted with EtOAc
  5. extractionThe extractions
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column (Eluent: PE/EtOAc=10:1)

출처 및 근거

ORD 기록
ord-e5995e6bb43b4cb283d58ea989579d1c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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