AZ20

(3R)-4-[2-(1H-indol-4-yl)-6-(1-methylsulfonylcyclopropyl)-4-pyrimidinyl]-3-methylmorpholine is a member of indoles.

4-{4-r(3R)-3-Methylmorpholin-4-yl1-6-ri-(methylsulfonyl)cvclopropyl1pyrimidin-2-yl}- lH-indoleBis(triphenylphosphine)palladium chloride (1.692 g, 2.41 mmol), (R)-4-(2-chloro-6-(l- (methylsulfonyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine (8.00 g, 24.11 mmol), IH- indol-4-ylboronic acid (4.27 g, 26.52 mmol) and 2M aqueous sodium carbonate (36.2 rnL, 72.33 mmol) were suspended in DME:water 4:1 (170 mL) and heated to 90 A mixture of (3R)-4-[2-chloro-6-(1-methanesulfonylcyclopropyl)pyrimidin-4-yl]-3-methylmorpholine 19(0.672 g, 2.02 mmol), (1H-indo-4-yl)boronic acid, 20 (1.14 g, 7.09 mmol), 1.2 M aqueous solution ofpotassium phosphate (6.08 mmol), and 1, 2-dimethoxyethane (15 mL) in 25 mL pressure flask wasdeoxygenated by passing a slow stream of nitrogen (about 50 mL/min) for 20 min. Then, XPhos PdG3 (0.10 g, 0.12 mol) was added in one portion. The flask was closed and the mixture was heated at70 °C with stirring for 20 h. The reaction mixture was diluted with 50 mL of EtOAc. The mixture waswashed with water (1x50 mL). The organics were separated; the aqueous solution was extracted withethyl acetate (3x50 mL). Combined organics were dried over magnesium sulfate, filtered andconcentrated in vacuo to afford crude product (about 1.0 g) as brown oil. The crude was purified onsilica (Biotage system, 40 g cartridge) with 0-30percent gradient of EtOAc/EtOH (4:1) in hexanes. Fractionscontaining product were combined, evaporated, and dried under vacuum to afford 21 as white solid(0.531 g, 64percent ). 1H NMR (400 MHz, DMSO-d6) δ 1.26 (d, J = 6.7 Hz, 3H), 1.60 (td, J = 5.7, 5.0, 3.5Hz, 2H), 1.71 (qd, J = 4.1, 3.4, 1.3 Hz, 2H), 3.22 (d, J = 3.9 Hz, 1H), 3.28 (s, 3H), 3.50 (td, J = 11.8, 3.0 Hz, 1H), 3.65 (dd, J = 11.5, 3.2 Hz, 1H), 3.78 (d, J = 11.4 Hz, 1H), 3.99 (dd, J = 11.4, 3.6 Hz, 1H), 4.20 (d, J = 13.5 Hz, 1H), 4.60 (s, 1H), 6.83 (s, 1H), 7.20 (t, J = 7.7 Hz, 1H), 7.31 (t, J = 2.6 Hz, 1H), 7.46 (t, J = 2.8 Hz, 1H), 7.54 (dd, J = 8.0, 1.0 Hz, 1H), 8.05 (dd, J = 7.5, 1.0 Hz, 1H), 11.28 (t, J = 2.3Hz, 1H). 13C NMR (101 MHz, DMSO-d6) δ 12.78, 13.87, 39.34, 40.81, 46.62, 46.87, 66.54, 70.71, 101.01, 103.33, 114.29, 120.92, 121.06, 126.75, 126.80, 129.84, 137.48, 161.99, 162.45, 164.94.MS-ESI m/z 413.26 [MH]+. Anal. Found (percent w/w): C, 61.27; H, 6.02; N, 13.42. C21H24N4O3S requiresC, 61.15; H, 5.86; N, 13.58. [α]23D -88.3 (c 1.03, DMSO).

Molecular Weight:412.5
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:412.15691181
Monoisotopic Mass:412.15691181
Topological Polar Surface Area:96.6
Heavy Atom Count:29
Complexity:707
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes