Triethylamine → HCID 67335125, compound

HRID 1670605Notes

Reaction equation

HRID 1670605 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH2:23])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH:23][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=2[N+:8]([O-:10])=[O:9])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 67335125HCID 67335125, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 5-bromo-2-fluoronitrobenzene (28.8 mmol, 3.55 mL), 3-amino-azetidine-1-carboxylic acid tert-butyl ester (28.8 mmol, 4.96 g), and triethylamine (35.9 mmol, 5.00 mL) in ethyl acetate (100 mL) and reflux under nitrogen for 48 h. Cool to room temperature. Wash with 0.5 M hydrochloric acid twice, dry over anhydrous sodium sulfate, filter, and concentrate in vacuo to obtain a bright orange solid (11.04 g, >100%). LC-MS m/z (79Br/81Br) 394.0/396.0 [M+H]+.

Workup

  1. temperaturereflux under nitrogen for 48 h
  2. washWash with 0.5 M hydrochloric acid twice
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-8518a09baf3241949ec27e517db3fc8a
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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