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

HRID 1508191Notes

Reaction equation

HRID 1508191 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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;

Workup

  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)

Sources & evidence

ORD record
ord-a391b02ed9834d7aac3e6b0926db75e4
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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