1,10-Phenanthroline → HCID 68380018, compound

HRID 2178675Notes

Reaction equation

HRID 2178675 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[S:16])[C:12]([F:15])([F:14])[F:13].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.[Cu](I)I>[CH3:9][O:8][C:7]1[C:2]2[S:16][C:11]([C:12]([F:15])([F:14])[F:13])=[N:10][C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 86671726HCID 86671726, compound

Product 1

HCID 68380018HCID 68380018, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroethanethioamide (C25) (748 mg, 2.38 mmol) in 1,2-dimethoxyethane (11.9 mL) was added 1,10-phenanthroline (88.4 mg, 0.48 mmol), cesium carbonate (1.55 g, 4.76 mmol), and copper iodide (45.3 mg, 0.24 mmol). Nitrogen was bubbled through the reaction for 30 minutes and the reaction was heated to 80° C. for 48 hours. The mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% diethyl ether in hexanes) afforded the title compound as a colorless solid. Yield: 398 mg, 1.71 mmol, 72%. GCMS m/z 233 (M+). 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 6.97 (br d, J=7.9 Hz, 1H), 7.56 (dd, J=8.3, 8.0 Hz, 1H), 7.82 (dd, J=8.3, 0.6 Hz, 1H).

Workup

  1. customNitrogen was bubbled through the reaction for 30 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography (Gradient: 0% to 30% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-2324dead8fb54fff8eb1aab993990195
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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