Water → HCID 89501539, compound

HRID 590540Notes

Reaction equation

HRID 590540 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>C(OC(=O)C)C>[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 69.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4 (500 mg, 3.85 mmol) in ethylacetate, triethylamine (973 mg, 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 dropwise 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 and the solvent is removed. The product is purified by column chromatography using hexanes-EtOAc mixtures to obtain the product as a crystalline yellow solid 9 (721 mg) in 70% isolated 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
  5. customthe solvent is removed
  6. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-1e2f53a0aac94e0a8a660d88714bea0e
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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