3-Hydroxypyridine → HCID 89581172, compound

HRID 1501156Notes

Reaction equation

HRID 1501156 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](O)[CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:10][C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 426142881-(5-Bromopyridin-2-yl)ethanol

Product 1

HCID 89581172HCID 89581172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(5-bromopyridin-2-yl)ethanol (600 mg, 3.00 mmol), pyridin-3-ol (283 mg, 2.98 mmol) and triphenyl phosphine (1.54 g, 5.88 mmol) was stirred in anhydrous tetrahydrofuran (20 mL) under nitrogen atmosphere. After stirring for 1 hour, the mixture was cooled to 0° C. Diisopropyl azodicarboxylate (658 mg, 3.26 mmol) was added dropwise and the reaction was stirred at room temperature for 18 hours. Then the solvent was evaporated and the residue was purified by column chromatography (silica gel, pure ether) to 5-bromo-2-(1-(pyridin-3-yloxy)ethyl)pyridine (744 mg, 89%). 1H NMR (300 MHz, CD3OD): δ 8.63-8.62 (m, 1H), 8.21-8.19 (m, 1H), 8.08-8.06 (m, 1H), 7.98-7.94 (m, 1H), 7.45 (d, J=5.1 Hz, 1H), 7.33-7.28 (m, 2H), 5.51 (q, J=6.3 Hz, 1H), 1.68 (d, J=6.3 Hz, 3H).

Workup

  1. stirringthe reaction was stirred at room temperature for 18 hours
  2. customThen the solvent was evaporated
  3. customthe residue was purified by column chromatography (silica gel, pure ether) to 5-bromo-2-(1-(pyridin-3-yloxy)ethyl)pyridine (744 mg, 89%)

Sources & evidence

ORD record
ord-41e56391cb434ce48297d2a79c0112a9
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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