Ethylenediamine → HCID 2989257, compound

HRID 911289Notes

Reaction equation

HRID 911289 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([F:15])[CH:3]=1.[Cu][C:17]#[N:18].C(N)CN>CN(C=O)C>[C:9]([NH:8][C:6](=[O:7])[C:5]1[CH:13]=[CH:14][C:2]([C:17]#[N:18])=[CH:3][C:4]=1[F:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 223362524-Bromo-N-tert-butyl-2-fluorobenzamideHCID 178418546HCID 178418546, compound

Product 1

HCID 2989257HCID 2989257, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-bromo-N-tert-butyl-2-fluoro-benzamide (1.0 g, 3.65 mmol) and copper(I) cyanide (0.7 g, 7.29 mmol) in anhydrous DMF (10 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature and treat with 50% (v/v) aqueous ethylenediamine (20 mL). Extract the reaction mixture with diethyl ether (3×10 mL), combine the organic extracts, wash with brine (2×10 mL) and dry the organic layer over Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2) to obtain the desired intermediate as a white solid (0.6 g, 77%). MS (ES+) m/z: 221 (M+H)+.

Workup

  1. extractionExtract the reaction mixture with diethyl ether (3×10 mL)
  2. washwash with brine (2×10 mL)
  3. dry with materialdry the organic layer over Na2SO4
  4. customEvaporate the solvent
  5. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2)

Sources & evidence

ORD record
ord-4a2103c3bf1b4d0ca95aadfb3e1a74c9
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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