Water → HCID 89501582, compound

HRID 590548Notes

Reaction equation

HRID 590548 reaction equation
Cl.[CH3:2][Si:3]1([CH3:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[C:20]([F:27])[C:19]=1F.O>CCOC(C)=O>[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[C:20]([F:27])[C:19]=1[N:6]1[CH2:7][CH2:8][Si:3]([CH3:9])([CH3:2])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27827931,2,3-Trifluoro-5-nitrobenzeneHCID 672158374,4-dimethyl-1,4-azasilinane hydrochloride

Product 1

HCID 89501582HCID 89501582, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4,4-dimethyl-1,4-azasilinane hydrochloride 4 (950 mg, 7.35 mmol) in EtOAc (15 mL), triethylamine (2.5 mL, 18.37 mmol) is added and stirred at 25° C. for 10 min. The reaction mixture is cooled to 0° C. and 1,2,3-trifluoro-5-nitrobenzene (1.29 g, 7.35 mmol) is added drop wise and allowed to stir at 25° C. for 6 h. Water is then added and the organic layer is separated. The aqueous layer is extracted with EtOAc (2×10 mL) and the solvent is removed under reduced pressure. The product obtained is purified by column chromatography using hexane-EtOAc mixtures to give the product as a crystalline yellow solid 9a (1.32 g) in 63% yield.

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. stirringto stir at 25° C. for 6 h
  3. customthe organic layer is separated
  4. extractionThe aqueous layer is extracted with EtOAc (2×10 mL)
  5. customthe solvent is removed under reduced pressure
  6. customThe product obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-c2e439b8f65848d0a2e12e74b70f0594
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

Loading…