Pyridine → HCID 10071889, compound

HRID 2181863Notes

Reaction equation

HRID 2181863 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:37])[CH2:35][CH3:36]>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:37])[CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 104300394-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol

Product 1

HCID 10071889HCID 10071889, compoundYield 77%

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, 0.06 g, 0.16 mmol) in dichloromethane (2 mL) was treated sequentially with pyridine (0.05 mL, 0.63 mmol) and propionyl chloride (0.03 mL, 0.3 mmol). After stirring for twelve hours at 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) to yield the title compound as a white solid (0.05, 77%), m.p. 111-112° C.;

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)

Sources & evidence

ORD record
ord-654c8bcf8f014864a319cdd8916e0815
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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