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

HRID 1363177Notes

Reaction equation

HRID 1363177 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a586cc6e393d43a7a2bf26dc3ee292de
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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