Cesium carbonate → HCID 86585865, compound

HRID 1005802Notes

Reaction equation

HRID 1005802 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N+:11]([O-:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[C:19](=O)([O-])[O-].[Cs+].[Cs+].C([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[SH:34])(C)C.[CH3:35][C:36](N(C)C)=O>>[CH:36]([C:4]1[C:3]([C:15]([F:18])([F:17])[F:16])=[C:2]([S:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:28]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][N+:11]([O-:14])=[CH:10][CH:9]=1)([CH3:35])[CH3:19]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 21906801Pyridine, 4-[4-fluoro-3-(trifluoromethyl)phenyl]-, 1-oxide

Product 1

HCID 86585865HCID 86585865, compoundYield 84%

Conditions

Temperature
100 °C

Procedure

Then, 4-(4-(2-isopropyl-phenylsulfanyl-3-trifluoromethyl-phenyl)-pyridine-1-oxide 75 was prepared as follows. A solution of compound 74 (2.51 g, 9.76 mmol) in dimethylacetamide (100 mL) was purged with nitrogen gas for 10 minutes. To it was added cesium carbonate (3.80 g, 11.7 mmol), followed by 2-isopropylthiophenol (4.90 mL, 29.3 mmol). The reaction was heated at 100° C. for 16 hours. The mixture was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was separated, washed with brine (5×200 mL), dried over MgSO4 and then filtered. After evaporating the solvent, the crude material was loaded to a silica gel column, eluting with 10% methanol in ethyl acetate to give a white solid 75 (3.19 g 84%). 1H-NMR (CDCl3, 400 MHz) δ 1.19 (d, J=6.8 Hz, 6H), 3.51 (heptaplet, J=6.8 Hz, 1H), 6.90 (d, J=8.1 Hz, 1H), 7.22-7.28 (m, 1H), 7.44-7.51 (m, 6H), 7.84 (d, J=2.1 Hz, 1H), 8.24 (d, J=7.4 Hz, 2H); MS (DCI) m/z 390 (M+H)+.

Workup

  1. customThen, 4-(4-(2-isopropyl-phenylsulfanyl-3-trifluoromethyl-phenyl)-pyridine-1-oxide 75 was prepared
  2. customThe mixture was partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (5×200 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customAfter evaporating the solvent
  8. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-691482a93e8d4866afdc04b3cbc13c7f
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

Loading…