Potassium Carbonate → HCID 11992772, compound

HRID 2241058Notes

Reaction equation

HRID 2241058 reaction equation
Br[CH2:2][C:3]#[N:4].[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[CH:9][C:8]=1[OH:30])C.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:5][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14]2[CH2:19][C:18]([CH3:20])([CH3:21])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[CH:9][C:8]=1[O:30][CH2:2][C:3]#[N:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68500262HCID 68500262, compound

Product 1

HCID 11992772HCID 11992772, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

Bromoacetonitrile (134 mg, 1.12 mmol), compound 41 (150 mg, 0.449 mmol), and K2CO3 (185 mg, 1.34 mmol) were combined with dry acetone (5 mL) in a sealed microwave vessel. The mixture was heated at 100° C. for 20 min in a Personal Chemistry Emrys Optimizer microwave. The reaction was allowed to cool to room temperature and the solids filtered. The solids were rinsed twice with acetone and the solvent removed in vacuuo. The crude mixture was purified using flash column chromatography with dichloromethane as the eluent to give 60 mg (36%) of 45 as a colorless solid (36%). 1H NMR (400 MHz, CDCl3): δ 0.88 (s, 6H), 0.91 (s, 6H), 1.25 (s, 2H), 1.77 (s, 2H), 1.90 (s, 2H), 2.20 (s, 3H), 4.62-4.68 (s, 2H), 6.78 (d, J=8.1 Hz, 1H) 6.75-7.05 (m, 2H), 7.09-7.25 (m, 5H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe solids filtered
  3. washThe solids were rinsed twice with acetone
  4. customthe solvent removed in vacuuo
  5. customThe crude mixture was purified

Sources & evidence

ORD record
ord-820d7fa3b7524869a3f7db93d9a7e6fb
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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