Tetrahydrofuran → HCID 22930006, compound

HRID 1296011Notes

Reaction equation

HRID 1296011 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[C:25]([C:33]#[N:34])=[N:26][C:27]([CH:30]2[CH2:32][CH2:31]2)=[CH:28][CH:29]=1)=[N+]=[N-].O1CCCC1>O>[CH:30]1([C:27]2[N:26]=[C:25]3[C:33]([NH2:34])=[N:20][CH2:23][C:24]3=[CH:29][CH:28]=2)[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 22929842HCID 22929842, compound

Product 1

HCID 22930006HCID 22930006, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenylphosphine (365 mg, 1.39 mmol) was added at room temperature to a solution of the 3-(azidomethyl)-6-cyclopropyl-2-pyridinecarbonitrile (230 mg, 1.15 mmol) in a tetrahydrofuran (4 ml) —H2O (0.2 ml) mixed solvent and the mixture was stirred for 3 hours. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography, to yield the title compound (180 mg, 90%) as a white amorphous solid from the ethyl acetate-methanol-29% NH3(aq) (30:10:1) elution fraction.

Workup

  1. additionmixed solvent
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1a4e7cef2d4d48e7b8c4006595ab7712
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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