تفاعل #1053675

معادلة التفاعل

DMF

5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester

K2CO3

→

indole-amine

المردود 50.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىThen the reaction was quenched with saturated sodium bicarbonate
2. 2
   استخلاصextracted with ethyl acetate (3×)
3. 3
   غسيلThe combined organic phases were washed with brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   أخرىAfter removing the solvent
6. 6
   أخرىchromatographed
7. 7
   غسيلeluting with ethyl acetate/methanol/triethyl amine (100/10/1)

الإجراء التجريبي

5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.300 g, 0.770 mmol, 1 eq, Example 56, Step D) was suspended in DMF (5 mL) under Ar. K2CO3 (0.425 g, 3.080 mmol, 4 eq) was added followed by the addition of (1S,4S)-(+)-1-Aza-5-oxabicycle[2,2,1]-heptane hydrochloride (0.314 g, 2.320 mmol, 3 eq). The reaction mixture was stirred at 80° C. for 18 hours. Then the reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic phases were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate/methanol/triethyl amine (100/10/1). 0.150 g (50%) of the indole-amine was obtained as a white solid. This was converted to the .HCl salt. LC/MS (ESI+) 391 (M+1); Anal. Calcd for C24H26N2O3.1HCl.0.90H2O: C, 65.05; H, 6.55; N, 6.32; Found: C, 65.05; H, 6.60; N, 6.13.

المصدر