2,2,2-Trifluoroethanol → HCID 71150638, compound

HRID 407242Notes

Reaction equation

HRID 407242 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].Br[C:14]1=[C:15]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[NH:16][CH:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[F:33])[CH2:18]/[C:19]/1=[N:20]\OS(C)(=O)=O>CCOCC>[NH2:20][C:19]1[CH:18]=[C:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[F:33])[N:16]=[C:15]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:14]=1[O:4][CH2:3][C:2]([F:6])([F:5])[F:1]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 178468457HCID 178468457, compound

Product 1

HCID 71150638HCID 71150638, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 2,2,2-trifluoroethanol (3.9 mL) and K2CO3 (54 mg, 3.9 mmol) was added (E)-ethyl 3-bromo-6-(4-chloro-2-fluorophenyl)-4-(((methylsulfonyl)oxy)imino)-1,4,5,6-tetrahydropicolinate (prepared as in Renga, J. M. et al. U.S. Patent Appl. Publ. 2010/0311594 A1, Dec. 9, 2010; 450 mg, 1 mmol). The mixture was stirred for 30 min, then diluted with Et2O and washed with 1 M HCl. The organic extracts were dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (eluting with 0-50% EtOAc/hexanes affording an off-white solid: (190 mg, 74%): mp 123-135° C.; 1H NMR (300 MHz, CDCl3) δ 8.00 (t, J=8.5 Hz, 1H), 7.23 (m, 3H), 7.15 (dd, J=11.1, 2.0 Hz, 1H), 4.59 (s, 2H), 4.46 (m, 4H), 1.44 (t, J=7.1 Hz, 3H); ESIMS m/z 393 ([M+H]+), 391 ([M−H]−).

Workup

  1. washwashed with 1 M HCl
  2. dry with materialThe organic extracts were dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (
  6. washeluting with 0-50% EtOAc/hexanes affording an off-white solid

Sources & evidence

ORD record
ord-807b1c174acb4526bf045a97826e3c9d
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

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