5-Fluoro-N,N-dimethyl-1H-indole-3-methanamine

5-Fluorogramine (7F)—A solution of 5-fluoroindole (1.0 g, 7.40 mmol) in 1 ml of AcOH was added to a solution of dimethylamine(567 mg, 1.42 ml, 12.58 mmol, 40percent aqueous solution)and formaldehyde (333 mg, 0.9 ml, 11.09 mmol, 37percent aqueoussolution) in 5 ml of acetic acid at 0 °C under an argon atmosphere.The mixture was stirred without cooling for 3 h, pouredonto 20 ml of ice-water, and adjusted to pH 11 with 2 M NaOH.The resulting suspension was extracted with diethyl ether and dried with MgSO4, and the solvent was evaporated underreduced pressure. Column chromatography on silica (CHCl3/MeOH/NH4OH 90:10:1 3 40:10:1) gave the product (1.33 g, 6.92 mmol, 93percent) as a beige-colored solid. 1H NMR (ppm) (400MHz, CDCl3): 8.47 (s, 1H), 7.36–7.31 (m, 1H), 7.25–7.20 (m, 1H), 7.12 (d, 3J 2.6, 1H), 6.95–6.88 (m, 1H), 3.58 (s, 2H), 2.28(s, 6H). 13CNMR(ppm) (100 MHz, CDCl3): 157.5 (d, 1J234.4, F-Cq), 132.4 (Cq), 128.0 (d, 3J 9.9, Cq), 125.1 (CHarom), 113.2(d, 4J 4.9, Cq), 111.3 (d, 3J 9.7, CHarom), 110.0 (d, 2J 26.4, CHarom), 103.87 (d, 2J 23.5, CHarom), 54.1 (-CH2-), 44.9(2x-CH3).

Molecular Weight:192.23
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:192.10627659
Monoisotopic Mass:192.10627659
Topological Polar Surface Area:19
Heavy Atom Count:14
Complexity:196
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes