3-Fluorobenzoyl chloride → HCID 71184872, compound

HRID 1629963Notes

Reaction equation

HRID 1629963 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](Cl)=[O:15].Cl.[Cl:21][C:22]1[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][N:23]=1>C(Cl)Cl>[Cl:21][C:22]1[CH2:26][C:25]([CH3:28])([CH3:27])[N:24]([C:14]([C:13]2[CH:17]=[CH:18][CH:19]=[C:11]([F:10])[CH:12]=2)=[O:15])[N:23]=1

Participants

5

Reactant 3

HCID 743763-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 89654102HCID 89654102, compound

Product 1

HCID 71184872HCID 71184872, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 250 mL round bottom flask equipped with a stir bar and nitrogen inlet was charged with dry CH2Cl2 (100 mL), Hunigs base (7.8 mL, 45 mmol) DMAP (5 mg) and 3-fluorobenzoyl chloride (1.8 mL. 15 mmol). The mixture was cooled to 0° C. To this mixture was added portionwise, 3-chloro-5,5-dimethyl-4,5-dihydro-1H-pyrazole.Hydrochloride (1.68 g, 10 mmol) and the reaction was allowed to warm to RT overnight. LC-MS showed consumption of SM. The reaction was added to water (100 mL), the phases were separated and the organic phase was washed with NaHCO3 (100 mL), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The material was purified by chromatography using a 40 g silica cartridge eluting with heptane-EtOAc, gradient 0 to 20% EtOAc. Amount obtained: 0.9 g, 3.7 mmol, 37% yield. LC-MS (ESI) m/e 255 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.76 (s, 6H) 3.03 (s, 2 H) 7.14 (td, J=8.36, 1.98 Hz, 1H) 7.36 (td, J=7.96, 5.71 Hz, 1H) 7.43 (dd, J=9.57, 2.25 Hz, 1H) 7.51 (d, J=7.76 Hz, 1H).

Workup

  1. customA 250 mL round bottom flask equipped with a stir bar and nitrogen inlet
  2. additionTo this mixture was added portionwise
  3. temperatureto warm to RT overnight
  4. customconsumption of SM
  5. additionThe reaction was added to water (100 mL)
  6. customthe phases were separated
  7. washthe organic phase was washed with NaHCO3 (100 mL)
  8. dry with materialdried (Na2SO4)
  9. customthe solvent was evaporated under reduced pressure
  10. customThe material was purified by chromatography
  11. washeluting with heptane-EtOAc, gradient 0 to 20% EtOAc
  12. customAmount obtained

Sources & evidence

ORD record
ord-6064ab48a940402e9ba339df9a706346
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

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