Sodium Azide → tert-Butyl 3-[3-(1-azidoethyl)-5-chloro-6-fluoro-2-methoxyphenyl]azetidine-1-carboxylate

HRID 510947Notes

Reaction equation

HRID 510947 reaction equation
[Cl:1][C:2]1[C:3]([F:24])=[C:4]([CH:13]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)[C:5]([O:11][CH3:12])=[C:6]([CH:8](Cl)[CH3:9])[CH:7]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C.CCOCC>[N:25]([CH:8]([C:6]1[C:5]([O:11][CH3:12])=[C:4]([CH:13]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)[C:3]([F:24])=[C:2]([Cl:1])[CH:7]=1)[CH3:9])=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86666861Tert-butyl 3-(3-chloro-5-(1-chloroethyl)-2-fluoro-6-methoxyphenyl)azetidine-1-carboxylate

Product 1

HCID 86666862tert-Butyl 3-[3-(1-azidoethyl)-5-chloro-6-fluoro-2-methoxyphenyl]azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 3-[3-chloro-5-(1-chloroethyl)-2-fluoro-6-methoxyphenyl]azetidine-1-carboxylate (0.070 g, 0.18 mmol) and sodium azide (0.036 g, 0.56 mmol) in DMF (0.66 mL) was stirred at room temperature overnight. After diluting with ether, the mixture was washed with water, dried over MgSO4 and concentrated to give the crude azide which was used in the next step without further purification. LCMS calculated for C17H22ClFN4O3Na (M+Na)+: m/z=407.1. found: 407.0.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c10f6ee78a45454e97912b8ec8954ba5
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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