HCID 15405369, compound → HCID 54527469, compound

HRID 363292Notes

Reaction equation

HRID 363292 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[C:9]([F:15])[C:10]([N+:12]([O-])=O)=[CH:11][C:6]=2[CH2:5][S:4]1(=[O:17])=[O:16])[CH3:2].[H][H]>O1CCCC1.[Pd]>[CH2:1]([N:3]1[C:7]2[CH:8]=[C:9]([F:15])[C:10]([NH2:12])=[CH:11][C:6]=2[CH2:5][S:4]1(=[O:17])=[O:16])[CH3:2]

Participants

5

Reactant 2

HCID 15405369HCID 15405369, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 54527469HCID 54527469, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-Ethyl-6-fluoro-1,3-dihydro-5-nitro-2,1-benzisothiazole 2,2-dioxide (Compound B from Example 1, Step C, 1.0 g), was suspended in tetrahydrofuran (20 mL) with 10% palladium on carbon (100 mg). The suspension was placed in Parr® shaker and treated with 50 psi (3.45×105Pa) of hydrogen overnight. The catalyst was then filtered off through diatomaceous earth (Celite®), and the filtrate was evaporated under reduced pressure to give the title compound of Step A as a brown solid (0.510 mg). 1H NMR (CDCl3): δ 6.92 (dd,1H), 6.04 (dd,1H), 4.08 (s,2H), 3.80 (br s,2H), 3.64 (q,2H), 1.32 (t,3H).

Workup

  1. filtrationThe catalyst was then filtered off through diatomaceous earth (Celite®)
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b8f28abe37a44f6c8023db89c5475ed9
Source dataset
uspto-grants-1999_02
Patent number
US05874382

Reaction notes

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