Ethylenediamine → HCID 2989257, compound

HRID 2041178Notes

Reaction equation

HRID 2041178 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-fc1d08ba683a41f19f995569852cc2d2
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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