Pyridine → HCID 10345344, compound

HRID 2181864Notes

Reaction equation

HRID 2181864 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:2].N1C=CC=CC=1.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[C:34]([O:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([N:4]2[CH:3]([CH2:1][CH3:2])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=3)[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)(=[O:20])=[O:19])=[CH:26][CH:25]=1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 104300394-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol

Product 1

HCID 10345344HCID 10345344, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol (Example 40, Step d, 0.05 g, 0.13 mmol) in dichloromethane (2 mL) was treated sequentially with pyridine (0.04 mL, 0.52 mmol) and benzoyl chloride (0.03 mL, 0.26 mmol). After stirring for twelve hours and room temperature, the reaction was quenched with a saturated, aqueous sodium bicarbonate solution (50 mL). The separated aqueous phase was extracted with dichloromethane (3×10 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude product. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 1:4 gradient), followed by re-crystallization from a mixture of ethyl acetate-hexane, to yield the title compound as a white solid (0.04 g, 59%);

Workup

  1. customthe reaction was quenched with a saturated, aqueous sodium bicarbonate solution (50 mL)
  2. extractionThe separated aqueous phase was extracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a crude product
  6. customThe crude product was purified by flash column chromatography on silica gel
  7. washeluting with a mixture of ethyl acetate-hexane (1:9 to 1:4 gradient)
  8. customfollowed by re-crystallization from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-93e5a11740c74c258b547418deb788ff
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…