Stannane, trimethyl(4-methylphenyl)- → 2'-(N-t-Butylsulfamoyl)-4-methylbiphenyl

HRID 1647926Notes

Reaction equation

HRID 1647926 reaction equation
Br[C:2]1([S:12]([NH2:15])(=[O:14])=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]1[C:8]([CH3:11])([CH3:10])C.[CH3:16][C:17]1[CH:22]=CC([Sn](C)(C)C)=C[CH:18]=1>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][C:3]1[CH:4]=[CH:10][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[S:12]([NH:15][C:17]([CH3:16])([CH3:18])[CH3:22])(=[O:13])=[O:14])=[CH:11][CH:2]=1

Participants

5

Reactant 2

HCID 617834Stannane, trimethyl(4-methylphenyl)-HCID 67773766HCID 67773766, compound

Product 1

HCID 152820992'-(N-t-Butylsulfamoyl)-4-methylbiphenylYield 116.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromo-2-t-butylbenzenesulfonamide (22.4 g, 77 mmol) (Step A) and 4-methylphenyltrimethylstannane (39.35 g, 154 mmol 2eq.) were dissolved in 221 mL of dry dimethylformamide and the resulting solution treated with 2.71 g (38.6 mmol, 0.5eq) of bis(triphenylphosphine)palladium(II) chloride. The mixture was heated at 90° C. for 6 hours. The mixture was filtered through Celite and the filter cake was washed with ether. The combined organics were washed twice with water. The aqueous washings were combined and extracted with ether. The combined organics were washed with saturated aqueous sodium chloride then dried over magnesium sulfate, filtered and concentrated to dryness to yield the product which solidified on standing. Purification by preparative HPLC on silica, eluting with 10% ethyl acetate/hexane, gave 13.63 g (44.98 mmol, 58%) of the product as a yellow powder. 1H NMR (200 MHz, CDCl3): δ 1.09 (s, 9H), 2.50 (s, 3H), 3.64 (br s, 1H), 7.3-7.7 (m,7H), 8.13 (dd; 2, 8 Hz; 1H). FAB-MS: calculated for C17H21NO2S 303; found 304 (M+H, 3%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with ether
  3. washThe combined organics were washed twice with water
  4. extractionextracted with ether
  5. washThe combined organics were washed with saturated aqueous sodium chloride
  6. dry with materialthen dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customto yield the product which
  10. customPurification by preparative HPLC on silica
  11. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-21ccfa2821ec48e2989a34bbe4c31065
Source dataset
uspto-grants-1995_07
Patent number
US05434261

Reaction notes

Loading…