2-Iodotoluene → HCID 9882866, compound

HRID 1859628Notes

Reaction equation

HRID 1859628 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH2:9]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]#N)[CH2:15][CH2:14]1)[CH2:10][CH2:11][CH3:12].C(O)(C(F)(F)F)=[O:25].CC#N>CCOCC.C(Cl)Cl>[CH2:9]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:8])=[O:25])[CH2:15][CH2:14]1)[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 51282-IodotolueneHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 186263654-(4-Butyl-piperazin-1-yl)-butyronitrile

Product 1

HCID 9882866HCID 9882866, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In a 10 mL oven-dried flask charged with Mg turnings (100 mg, 4.0 mmol) which was activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a suspension of 2-iodotoluene (0.66 g, 3.0 mmol) in Et2O (3 mL) and the reaction mixture was allowed to reflux for 1 hours. A suspension of compound 16 (0.43 g, 2.0 mmol) in CH2Cl2 (3 mL) was added via a syringe and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (6 mL, 2 M) and stirred at rt for 2 hours followed by addition of NaOH (8 mL, 2 M). Addition of THF (15 mL) was followed by extraction with CH2Cl2 (3×20 mL), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.50 g of crude 17. The crude product was subjected to preparative HPLC [eluent:,Buffer A: 0.1% TFA; Buffer B: 80% CH3CN+0.1% TFA] to produce an analytical pure sample of compound 17. LC-MS [M+H]+ 302 (cald. 302.5).

Workup

  1. customIn a 10 mL oven-dried flask
  2. additionUnder inert atmosphere was added
  3. temperatureto reflux for 1 hours
  4. additionwas added via a syringe
  5. customThe reaction mixture was quenched by addition of H2SO4 (6 mL, 2 M)
  6. stirringstirred at rt for 2 hours
  7. additionfollowed by addition of NaOH (8 mL, 2 M)
  8. additionAddition of THF (15 mL)
  9. extractionwas followed by extraction with CH2Cl2 (3×20 mL)
  10. dry with materialthe organic phases were dried (MgSO4)
  11. customevaporated to dryness
  12. customto produce 0.50 g of crude 17

Sources & evidence

ORD record
ord-ee407177b1bd45c3b66dded342763576
Source dataset
uspto-grants-2003_03
Patent number
US06528529B1

Reaction notes

Loading…