HCID 86585865, compound → HCID 86585866, compound

HRID 1005803Notes

Reaction equation

HRID 1005803 reaction equation
[CH:1]([C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:5]=1[C:21]1[CH:26]=[CH:25][N+:24]([O-])=[CH:23][CH:22]=1)([CH3:3])[CH3:2]>O=P(Cl)(Cl)Cl>[CH:1]([C:4]1[C:9]([C:10]([F:13])([F:11])[F:12])=[C:8]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:5]=1[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 86585865HCID 86585865, compound

Product 1

HCID 86585866HCID 86585866, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Then, 2-chloro-4-(4-(2-isopropyl-phenylsulfanyl-3-trifluoromethyl-phenyl)-pyridine 76 was prepared as follows. Compound 75 (3.19 g, 8.19 mmol) was treated with POCl3 (50 mL) at 100° C. for 10 hours. The reaction mixture was concentrated on a rotovap, and the residue was treated with crushed ice (20 g). Water (100 mL) was added, the aqueous solution was then extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (3×100 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography to give the title compound 76 as a brown oil (2.74 g, 82%). 1H-NMR (CDCl3, 400 MHz) δ 1.19 (d, J=6.8 Hz, 6H), 3.51 (heptet, J=6.8 Hz, 1H), 6.91 (d, J=8.5 Hz, 1H), 7.25-7.28 (m, 1H), 7.37 (dd, J=1.7 Hz, 5.1 Hz, 1H), 7.45-7.52 (m, 5H), 7.87 (d, J=2.0 Hz, 1H), 8.43 (d, J=5.4 Hz, 1H). MS (DCI) m/z 408, 409, 410 (M+H)+.

Workup

  1. customThen, 2-chloro-4-(4-(2-isopropyl-phenylsulfanyl-3-trifluoromethyl-phenyl)-pyridine 76 was prepared
  2. concentrationThe reaction mixture was concentrated on a rotovap
  3. additionthe residue was treated with crushed ice (20 g)
  4. additionWater (100 mL) was added
  5. extractionthe aqueous solution was then extracted with ethyl acetate (2×100 mL)
  6. washThe combined organic layers were washed with brine (3×100 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-2af62c34a7094e7891ebc0b249ea871c
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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