HCID 86687720, compound → HCID 86687732, compound

HRID 1473658Notes

Reaction equation

HRID 1473658 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([O:21][C:22]4[C:27]([F:28])=[C:26]([F:29])[C:25]([F:30])=[C:24]([F:31])[C:23]=4[F:32])(=[O:20])=[O:19])=[CH:15][CH:16]=3)[C:11](=[O:33])[NH:10][N:9]=2)[CH:7]=1>[Pd]>[CH3:35][O:34][C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([O:21][C:22]3[C:23]([F:32])=[C:24]([F:31])[C:25]([F:30])=[C:26]([F:29])[C:27]=3[F:28])(=[O:19])=[O:20])=[CH:15][CH:16]=2)[C:11](=[O:33])[NH:10][N:9]=1

Participants

3

Reactant 1

HCID 86687720HCID 86687720, compound

Product 1

HCID 86687732HCID 86687732, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
75 °C

Procedure

A RBF was charged with perfluorophenyl 1-(5-chloro-2-methoxyphenyl)-4-oxo-3,4-dihydrophthalazine-6-sulfonate (1.25 g, 2.35 mmol). The reaction was purged with N2. Then ethyl acetate (23.5 mL) was added followed by palladium, 10 wt % on activated carbon (0.749 g, 0.704 mmol). The flask was evacuated and back filled with N2 (3×). The flask was evacuated again and then pressurized with hydrogen to 42 PSI. The reaction was heated to 75° C. After 2 d, LCMS showed 92:8 ratio of product:SM. The reaction was cooled to rt and filtered through a pad of Celite with the aid of EtOAc. The filtrate was concentrated. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (80 g), eluting with a gradient of 0% to 30% EtOAc in heptane, to provide perfluorophenyl 1-(2-methoxyphenyl)-4-oxo-3,4-dihydrophthalazine-6-sulfonate (613 mg, 52.4% yield) as off-white solid. m/z (ESI) 499.0 (M+H)+.

Workup

  1. customThe reaction was purged with N2
  2. additionThen ethyl acetate (23.5 mL) was added
  3. customThe flask was evacuated
  4. additionback filled with N2 (3×)
  5. customThe flask was evacuated again
  6. temperatureThe reaction was cooled to rt
  7. filtrationfiltered through a pad of Celite with the aid of EtOAc
  8. concentrationThe filtrate was concentrated
  9. customThe crude material was absorbed onto a plug of silica gel
  10. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (80 g)
  11. washeluting with a gradient of 0% to 30% EtOAc in heptane

Sources & evidence

ORD record
ord-90d8c5a44ab84b618cb659839dfc5c9a
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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