1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(Azidomethyl)-5-bromopyridine

HRID 2060077Notes

Reaction equation

HRID 2060077 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.C1(P([N:24]=[N+:25]=[N-:26])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1COCC1>[N:24]([CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 576405383-(Azidomethyl)-5-bromopyridineYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-bromo-pyridin-3-yl)-methanol 249 (1.4 g, 7.5 mmol, 1.00 equiv) and diphenylphosphoryl azide (2.4 mL, 9.0 mmol, 1.2 equiv) in THF (15 mL) at it was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.4 mL, 9.0 mmol, 1.2 equiv). The resulting solution was stirred overnight, concentrated and chromatographically purified (15% ethyl acetate in hexanes) to give 3-azidomethyl-5-bromo-pyridine 250 (1.49 g). LCMS (MH)+=212.9, rt=1.50 min.

Workup

  1. concentrationconcentrated
  2. customchromatographically purified (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8947559825f64ab7a82ed791aaaa5d1b
Source dataset
uspto-grants-2012_10
Patent number
US08278337B2

Reaction notes

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