Reaktion #71307

Reaktionsgleichung

N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

sodium carbonate

methanol

→

title compound

Ausbeute 22.0%

Methyl 1-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

Ausbeute 22.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter this time, catalyst and Na2CO3 were filtered off
2. 2
   workup.STIRRINGthe reaction was stirred for 24 hr at 100° C.
3. 3
   FiltrationThe mixture was filtered
4. 4
   Sonstigepartitioned between EtOAc and brine, organic layer
5. 5
   Sonstigeseparated
6. 6
   Waschenwashed with brine
7. 7
   workup.ADDITIONTo the organic layer was added silica and Na2SO4
8. 8
   workup.ADDITIONadded
9. 9
   workup.STIRRINGstirred for 20 min
10. 10
    FiltrationThe whole was filtered
11. 11
    Sonstigesolvent evaporated in vacuo
12. 12
    Sonstigeto give a brown oil
13. 13
    SonstigePurification by flash chromatography (0-50% EtOAc in heptane)

Vorschrift

A 150 mL steel autoclave was charged with N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (4.85 g, 15.24 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium(II)dichloride (0.622 g, 0.762 mmol), and sodium carbonate (3.23 g, 30.5 mmol) in degassed methanol. The autoclave was placed under carbon monoxide atmosphere (12 bar) and stirred at 100° C. for 24 hr. After this time, catalyst and Na2CO3 were filtered off and replaced with a new batch and the reaction was stirred for 24 hr at 100° C. and 12 bar CO. The mixture was filtered and partitioned between EtOAc and brine, organic layer separated, washed with brine. To the organic layer was added silica and Na2SO4 added and stirred for 20 min. The whole was filtered and solvent evaporated in vacuo to give a brown oil. Purification by flash chromatography (0-50% EtOAc in heptane) afforded the title compound as a yellow/brown oil (1 g, 22%). 1H NMR (400 MHz, CDCl3) δ 1.46 (d, 6H) 1.95 (m, 1H) 2.65 (m, 1H) 2.85 (m, 1H) 3.00 (m, 1H) 3.25 (m, 1H) 3.91 (s, 3H) 4.25 (d, 1H) 5.00 (q, 1H) 7.50 (d, 1H) 7.90 (m, 2H).

Quelle