HCID 58531544, compound → HCID 58531635, compound

HRID 1889701Notes

Reaction equation

HRID 1889701 reaction equation
[Cl:1][C:2]1[C:3]([OH:37])=[C:4]([S:9]([N:12]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH2:13][C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[CH:17]=[CH:18][CH:19]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1>C(O)(=O)C.[Fe]>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][N:12]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[S:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=3[OH:37])(=[O:11])=[O:10])[CH:15]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 58531544HCID 58531544, compound

Product 1

HCID 58531635HCID 58531635, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxy-N-((4′-nitrobiphenyl-3-yl)-methyl)benzenesulfonamide (0.2 g, 0.4 mmol) and iron (0.1 g, 2.1 mmol) in acetic acid (5 mL) was heated at 70° C., under a nitrogen atmosphere. After 40 minutes, the reaction mixture was cooled to room temperature and filtered through a pad of Celite®. The pad was thoroughly rinsed with EtOAc followed by CHCl3. The combined filtrates were concentrated in vacuo. The crude product was dissolved in CHCl3 then passed through a RediSep normal phase silica flash column (12 g) eluting with CHCl3. The appropriate fractions were concentrated in vacuo to afford the title compound (0.18 g, 84%) as an off-white solid. 1H NMR (DMSO-d6) δ 7.77 (d, J=2.2 Hz, 1H), 7.58 (d, J=2.7 Hz, 1H), 7.34 (d, J=7.7 Hz, 1H), 7.24-7.03 (m, 8H), 6.93 (d, J=7.7 Hz, 1H), 6.63-6.58 (m, 2H), 4.46 (s, 2H), 4.43 (s, 2H). MS (ESI): 531.0 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of Celite®
  3. washThe pad was thoroughly rinsed with EtOAc
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. dissolutionThe crude product was dissolved in CHCl3
  6. washeluting with CHCl3
  7. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-c9cf5cf45f244333a0fd9abf7fe303ee
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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