2,4,6-Trimethylpyridine → HCID 123349683, compound

HRID 718145Notes

Reaction equation

HRID 718145 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[NH:14])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1.N1C(C)=CC(C)=CC=1C.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)Cl>[CH2:28]([O:27][C:25]([N:14]=[C:10]([O:11][CH2:12][CH3:13])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=1)=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 10928Ethyl chloroformateHCID 13780008HCID 13780008, compound

Product 1

HCID 123349683HCID 123349683, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(4-fluorophenyl)acetimidate hydrochloride (1.6 g, 7.4 mmol) was suspended in hexanes (18.5 mL) and DCM (18.5 mL) at 0° C. 2,4,6-collidine (3.9 mL, 29.6 mmol) and ethyl chloroformate (1.6 g, 14.8 mmol) were added sequentially and the reaction mixture was allowed to warm to RT and stirred for 12 h. The solvent was removed in vacuo and the residue was suspended in EtOAc (100 mL) and sonicated for 10 minutes. The solids were removed by filtration through a pad of diatomaceous earth and the filter cake was washed with EtOAc (3×10 mL). The combined filtrates were concentrated in vacuo to afford ethyl N-ethoxycarbonyl-2-(4-fluorophenyl)acetimidate (0.99 g, 52.7%) as an amorphous yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 7.25 (dd, J=8.5, 5.6 Hz, 2H), 7.13 (t, J=8.8 Hz, 2H), 4.06 (q, J=7.1 Hz, 2H), 4.04 (q, J=7.1 Hz, 2H), 3.66 (s, 2H), 1.15 (t, J=7.1 Hz, 3H), 1.14 (t, J=7.1 Hz, 3H).

Workup

  1. customat 0° C
  2. customThe solvent was removed in vacuo
  3. customsonicated for 10 minutes
  4. customThe solids were removed by filtration through a pad of diatomaceous earth
  5. washthe filter cake was washed with EtOAc (3×10 mL)
  6. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-6d20aee15956492ca2563ebcb1908a50
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

Loading…