Water → HCID 89501539, compound

HRID 590544Notes

Reaction equation

HRID 590544 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:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1F.O>CCOC(C)=O>[F:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=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 1230531,2-Difluoro-4-nitrobenzeneHCID 672158374,4-dimethyl-1,4-azasilinane hydrochloride

Product 1

HCID 89501539HCID 89501539, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4,4-dimethyl-1,4-azasilinane hydrochloride 4 (500 mg, 3.85 mmol) in EtOAc (15 mL), triethylamine (1.3 mL, 9.63 mmol) is added and stirred at 25° C. for 10 min. The reaction mixture is cooled to 0° C. and 3,4-difluoronitrobenzene (612 mg, 3.85 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 is purified by column chromatography using hexane-EtOAc mixtures and a crystalline yellow solid 9 (721 mg) is obtained in 70% 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 is purified by column chromatography

Sources & evidence

ORD record
ord-17d4a825683f42adb6d6ab8cc3eb23fd
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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