1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-azido-3,4-dihydro-2H-pyrano[2,3-b]pyridine

HRID 1508191노트

반응식

HRID 1508191 반응식
[O:1]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[CH:4](O)[CH2:3][CH2:2]1.C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:26]([CH:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[O:1][CH2:2][CH2:3]1)=[N+:27]=[N-:28]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 230491373,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol

생성물 1

HCID 598465164-azido-3,4-dihydro-2H-pyrano[2,3-b]pyridine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol (3.31 mmol) in 16.5 mL toluene were added DPPA (4.96 mmol) followed by DBU (4.96 mmol) at 0° C. The cooling bath was removed after 2 h and the mixture was stirred at RT overnight. The reaction was quenched by adding sat. aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (4/1) to EtOAc gives the desired product as colorless oil;

후처리

  1. customThe cooling bath was removed after 2 h
  2. customThe reaction was quenched
  3. additionby adding sat. aq. NaHCO3 solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by CC (KP-SIL™ from Biotage)

출처 및 근거

ORD 기록
ord-a391b02ed9834d7aac3e6b0926db75e4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221832B2

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