HCID 67174946, compound → HCID 67311833, compound

HRID 1256066Notes

Reaction equation

HRID 1256066 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:11]([NH:14][C:15]1[C:16]([F:25])=[CH:17][C:18]2[CH2:22][O:21][B:20]([OH:23])[C:19]=2[CH:24]=1)(=[O:13])=[O:12].[H][H]>O1CCOCC1.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:11]([NH:14][C:15]2[C:16]([F:25])=[CH:17][C:18]3[CH2:22][O:21][B:20]([OH:23])[C:19]=3[CH:24]=2)(=[O:12])=[O:13])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 67174946HCID 67174946, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67311833HCID 67311833, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-fluoro-N-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide (1.84 g, 4.97 mmol) in 50 mL of dioxane was added Pd/C (10 wt. % on activated carbon, 500 mg). The reaction mixture was hydrogenated at room temperature under 50 psi of hydrogen for 16 hours. After Pd/C was filtered through a pad of Celite, the solution was concentrated under reduced pressure to give a yellow residue. The crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give 0.88 g of the title compound as a white solid. MS calcd for (C13H11BF2N2O4S): 340.1. MS found (ESI negative): (M−H)−=339.1. 1H NMR (DMSO-d6) δ (ppm): 9.69 (s, 1H), 9.23 (bs, 1H), 7.58 (d, 1H), 7.10-7.21 (m, 3H), 6.67 (t, 1H), 4.83 (s, 2H).

Workup

  1. filtrationAfter Pd/C was filtered through a pad of Celite
  2. concentrationthe solution was concentrated under reduced pressure
  3. customto give a yellow residue
  4. customThe crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-f8c5f2a4dbba49b6bc9333c2a3260ff3
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…