تفاعل #51536

معادلة التفاعل

H2O

(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole

4-chloro-1-(4-fluorophenyl)butan-1-one

K2CO3

→

title compound

المردود 67.0%

4-(7bR,11aS)-(1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-9(8H)-yl)-1-(4-fluorophenyl)-1-butanone

المردود 67.0%

المذيبات

1,4-dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   استخلاصextracted with EtOAc (2×20 mL)
3. 3
   تجفيفThe combined extracts were dried over magnesium sulfate
4. 4
   تركيزconcentrated
5. 5
   أخرىpurified by flash chromatography

الإجراء التجريبي

To a solution of (7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole from EXAMPLE 1 (80 mg, 0.32 mmol) in 1,4-dioxane (15 ml) at 25° C. was added 4-chloro-1-(4-fluorophenyl)butan-1-one (96 mg, 0.48 mmol), K2CO3 (100 mg, 0.72 mmol), and KI (32 mg, 0.19 mmol), respectively. The mixture was stirred at ambient temperature for 16 hours before H2O (10 mL) was added and then extracted with EtOAc (2×20 mL). The combined extracts were dried over magnesium sulfate, concentrated, and purified by flash chromatography to give the title compound of EXAMPLE 4 as an oil (88 mg, 67%). 1H NMR (CDCl3, 300 MHz): δ 8.01 (m, 2H), 7.15 (m, 2H), 6.96 (d, 1H, J=6.6 Hz), 6.92 (d, 1H, J 6.6 Hz), 3.82 (m, 2H), 3.25 (m, 2H), 3.19-2.60 (m, 8H), 2.42 (m, 2H), 1.95 (m, 5H). LRMS (ES)+: 411 (M+H)+.

المصدر