ACCEPTED MANUSCRIPT
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160.97, 160.48, 158.53, 144.97, 141.64, 137.94, 131.96, 131.92, 129.90, 129.57, 129.06, 128.98,
127.70, 126.93, 125.21, 124.75, 124.52, 123.90, 123.87, 115.58, 115.37, 50.43, 25.63, 24.57
ppm. HRMS (ESI) calculated for C26H23ClFN2 (M+H)+ 417.1528, found for 417.1525.
4.2.36 6-chloro-4-(2-fluorophenyl)-3-methyl-2-(4-methylpiperazin-1-yl)quinoline (F2a)
To a solution of A2a (0.156 mL, 0.001 mol) in dry chloroform (5 mL), POCl3 (0.153 mL, 0.001
mol) was added and the mixture was stirred at room temperature for 24 h. To this mixture, BA3
(0.292 g, 0.001 mol) was added and was refluxed till the reactants were consumed (checked
using TLC up to 48 h). A yellow solid was obtained which was crystallized from ethyl acetate.
Yield: 78%. MP = 170-172°C. FTIR (KBr): νmax = 3054.42; 2962.76; 2887.53; 1566.25;
1
1492.95; 1408.15; 1259.56; 831.35. H NMR (200 MHz, CDCl3):
δ
= 7.60 – 7.10 (m, 7H); 3.35
= 160.34,
(t, 4H); 2.90 (t, 4H); 2.40 (s, 3H); 2.10 (s, 3H). 13C NMR (101 MHz, CDCl3):
δ
159.99, 157.54, 143.38, 140.92, 130.60, 129.65, 128.85, 128.62, 128.25, 124.93, 124.19, 123.83,
123.72, 123.15, 115.51, 115.29, 54.37, 48.83, 45.40, 15.97 ppm. HRMS (ESI) calculated for
C21H22ClFN3 (M+H)+ 370.1481, found for 370.1475.
4.2.37 6-chloro-4-(2-fluorophenyl)-2-(4-methylpiperazin-1-yl)-3-phenyl-quinoline (F2b)
To a solution of A2b (0.219 mL, 0.001 mol) in dry chloroform (5 mL), POCl3 (0.153 mL, 0.001
mol) was added and the mixture was stirred at room temperature for 24 h. To this mixture, BA3
(0.292 g, 0.001 mol) was added and was refluxed till the reactants were consumed (checked
using TLC up to 48 h). A yellow solid was obtained which was crystallized from ethyl acetate.
Yield: 77%. MP = 227-228°C. FTIR (KBr): νmax = 3061.13; 2935.76; 1564.32; 1479.45;
1444.73; 1410.01; 1294.28; 696.33. 1H NMR (200 MHz, CDCl3):
δ
=7.40 – 7.15 (m, 12H); 3.65
δ = 159.21, 158.70, 148.26,
13
(t, 4H); 2.40 (t, 4H); 2.25 (s, 3H). C NMR (101 MHz, CDCl3):
146.55, 138.04, 137.31, 132.14, 130.64, 130.13, 129.04, 128.28, 127.70, 127.62, 126.44, 126.99,
126.90, 126.47, 126.44, 125.57, 124.85, 123.67, 116.89, 116.16, 54.88, 48.88, 46.08 ppm.
HRMS (ESI) calculated for C26H24ClFN3 (M+H)+ 432.1637, found for 432.1631.
4.2.38 6-chloro-2-(4-ethylpiperazin-1-yl)-4-(2-fluorophenyl)-3-methyl-quinoline (F3a)
To a solution of A3a (0.171 mL, 0.001 mol) in dry chloroform (5 mL), POCl3 (0.153 mL, 0.001
mol) was added and the mixture was stirred at room temperature for 24 h. To this mixture, BA3
(0.292 g, 0.001 mol) was added and was refluxed till the reactants were consumed (checked
using TLC up to 48 h). A yellow solid was obtained which was crystallized from ethyl acetate.
Yield: 74%. MP = 180-181°C. FTIR (KBr): νmax = 3053.42; 2968.55; 2929.97; 1577.82;