4-azido-3,4-dihydro-2H-pyrano[2,3-b]pyridine → 3,4-Dihydro-2H-pyrano[2,3-B]pyridin-4-amine

HRID 1363177노트

반응식

HRID 1363177 반응식
[N:1]([CH:4]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+]=[N-]>CO.[Pd]>[O:7]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[CH:4]([NH2:1])[CH2:5][CH2:6]1

참가 물질

4

반응물 1

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

생성물 1

HCID 598463753,4-Dihydro-2H-pyrano[2,3-B]pyridin-4-amine수율 97.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A catalytic amount of Pd/C (9 mg) was added to a solution of 4-azido-3,4-dihydro-2H-pyrano[2,3-b]pyridine (88 mg) in MeOH (5 mL). The flask closed with a septum, evacuated under house vacuum and hydrogen added via balloon. The resulting suspension was stirred at RT for 60 min, when the H2 balloon was removed, the mixture evacuated and filtered through a plug of celite, that was thoroughly rinsed with MeOH. Removal of the solvents gave the titled compound (73 mg), NMR CDCl3 1H δ 8.1 (dd, 1H), 7.7 (dd, 1H), 6.9 (dd, 1H), 4.5-4.3 (m, 2H), 4.1 (dd, 1H), 2.2 (m, 1H), 1.9 (m, 1H), 1.6 (br s, 2H); MH+=151.

후처리

  1. customThe flask closed with a septum
  2. customevacuated under house vacuum and hydrogen
  3. additionadded via balloon
  4. customwhen the H2 balloon was removed
  5. customthe mixture evacuated
  6. filtrationfiltered through a plug of celite, that
  7. washwas thoroughly rinsed with MeOH
  8. customRemoval of the solvents

출처 및 근거

ORD 기록
ord-a586cc6e393d43a7a2bf26dc3ee292de
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884109B2

반응 노트

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