반응 #71307

반응 방정식

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

sodium carbonate

methanol

→

title compound

수율 22.0%

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

수율 22.0%

반응 조건

후처리

1. 1
   여과After this time, catalyst and Na2CO3 were filtered off
2. 2
   workup.STIRRINGthe reaction was stirred for 24 hr at 100° C.
3. 3
   여과The mixture was filtered
4. 4
   기타partitioned between EtOAc and brine, organic layer
5. 5
   기타separated
6. 6
   세척washed 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
    여과The whole was filtered
11. 11
    기타solvent evaporated in vacuo
12. 12
    기타to give a brown oil
13. 13
    기타Purification by flash chromatography (0-50% EtOAc in heptane)

실험 절차

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).

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