Sodium Azide → 2-(2-Azido-1,1-difluoro-ethyl)-5-methyl-pyridine

HRID 1987048Notes

Reaction equation

HRID 1987048 reaction equation
[F:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)([F:5])[CH2:3]I.[N-:13]=[N+:14]=[N-:15].[Na+]>CS(C)=O>[N:13]([CH2:3][C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)([F:5])[F:1])=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57722708Pyridine, 2-(1,1-difluoro-2-iodoethyl)-5-methyl-

Product 1

HCID 577227242-(2-Azido-1,1-difluoro-ethyl)-5-methyl-pyridineYield 92.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-(1,1-Difluoro-2-iodo-ethyl)-5-methyl-pyridine (3.8 g, 13.43 mmol), as prepared in the previous step, was dissolved into DMSO (6 mL), treated with NaN3 (1.0 g, 16.12 mmol, 1.2×) and heated to 90° C. After 2 days, the reaction was partitioned between EtOAc (125 mL) and H2O (2×50 mL). The organic phase was dried over Na2SO4 and concentrated to afford the product as a clear oil (2.46 g, 12.42 mmol, 93% crude yield). 1H NMR (300 Hz, CDCl3) δ 8.49 (s, 1H), 7.63 (m, 2H), 4.01 (t, J=13.2 Hz), 2.41 (s, 3H); LC/MS (m/z) [M+1−N2]+ 171.1 (calculated for C8H9F2N2, 171.2).

Workup

  1. customthe reaction was partitioned between EtOAc (125 mL) and H2O (2×50 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5c5221efad3c4109a01ad2511b78ad1e
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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