Cesium carbonate → tert-Butyl 3-(6-Nitropyridin-3-yloxy)azetidine-1-carboxylate

HRID 1021936Notes

Reaction equation

HRID 1021936 reaction equation
I[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[N+:13]([C:16]1[N:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[N+:13]([C:16]1[N:21]=[CH:20][C:19]([O:22][CH:2]2[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27628576-Nitropyridin-3-olHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 1

HCID 58043652tert-Butyl 3-(6-Nitropyridin-3-yloxy)azetidine-1-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 206a (2.24 g, 7.9 mmol), 6-nitropyridin-3-ol (1.0 g, 7.2 mmol), and Cs2CO3 (2.6 g, 7.9 mmol) in DMF (8 mL) was heated at 125° C. in a sealed tube overnight. The solid was filtered and washed with ethyl acetate (2×20 mL). The combined filtrate was evaporated in vacuo and the residue was purified on reverse-phase Combiflash to afford 206b (1.25 g, 59%). MS-ESI: [M+H]+ 296.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with ethyl acetate (2×20 mL)
  3. customThe combined filtrate was evaporated in vacuo
  4. customthe residue was purified on reverse-phase Combiflash

Sources & evidence

ORD record
ord-f0b7d480b3ad4b778bfed5251dcbe17b
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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