1,2,3-Trifluoro-4-nitrobenzene → HCID 90036829, compound

HRID 1055393Notes

Reaction equation

HRID 1055393 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([N:18]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:19]([C:23]1([OH:29])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[C:20]([OH:22])=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.F[C:38]1[C:43]([F:44])=[C:42]([F:45])[CH:41]=[CH:40][C:39]=1[N+:46]([O-:48])=[O:47].OS([O-])(=O)=O.[K+]>C1COCC1.O>[CH2:30]([N:18]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:19]([C:23]1([O:29][C:38]2[C:43]([F:44])=[C:42]([F:45])[CH:41]=[CH:40][C:39]=2[N+:46]([O-:48])=[O:47])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[C:20]([OH:22])=[O:21])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 516920Potassium bisulfateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 72712772HCID 72712772, compound

Product 1

HCID 90036829HCID 90036829, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Potassium bis(trimethylsilyl) amide, 1 M solution in THF (4.22 mL, 4.22 mmol, Eq: 3.00), was added to a solution of 2-(dibenzylamino)-2-(4-hydroxytetrahydro-2H-pyran-4-yl)-acetic acid (0.5 g, 1.41 mmol, Eq: 1.00) in THF (10 mL) at RT and the mixture stirred for 15 min. The mixture was cooled to 0° C., 2,3,4-trifluoronitrobenzene (1.25 g, 0.83 mL, 7 mmol, Eq: 5.00) was added and the mixture stirred at 0° C. for 45 min. The mixture was diluted with H2O at 0° C. and was warmed to RT. The pH was adjusted to ˜2-3 with sat KHSO4, the mixture extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, concentrated and the residue purified by flash chromatography to afford 2-(dibenzylamino)-2-(4-(5,6-difluoro-2-nitrophenoxy)tetrahydro-2H-pyran-4-yl)-acetic acid (0.23 g, 32% yield). MS m/z 513.0 (MH+)

Workup

  1. stirringthe mixture stirred at 0° C. for 45 min
  2. temperaturewas warmed to RT
  3. extractionthe mixture extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-5e42496789ba445e92a051be70a325cf
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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