2-CHLORO-6-(TRIFLUOROMETHYL)BENZALDEHYDE

(5.3 g, 25.39 mmol) was added to a solution of 1H-pyrrolo[2, 3-b]pyridine (3g, 25.39 mmol) in methanol (125 mL) and stirred at rt followed bythe addition of a solution of potassium hydroxide (4.27 g, 76.18 mmol) in methanol (125 mL). The reaction was stirred at rt for 3 nights then concentrated toafford an orange oil which was partitioned between water (100 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (2 x 40 mL), combined and washed with water (3 x 50 mL), brine (5 mL), dried using Mg504, filtered and evaporated to dryness to afford 8g of colourless oil. The crude material was purified by FCC eluting in a gradient of 0-100% EtOAc in heptanes to afford 3.47g (40% yield) desired product [2-chloro-6-(trifluoromethyl) phenyl]( 1 H-pyrrolo[2 , 3-b]pyridin-3- yl)methanol as a white solid. 1H NMR (500 MHz, Chloroform-d) 6 9.21 (s, IH), 8.31(dd, J = 4.8, 1.5 Hz, 1H), 7.90 (dd, J = 7.9, 1.4 Hz, 1H), 7.74 (d, J = 7.3 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.06 (dd, J = 7.9, 4.8 Hz, 1H), 6.86 (dd, J = 2.2, 1.4 Hz, 1H), 6.62 (d, J = 4.9 Hz, 1H), 3.51 (5, 1H). LC/MS (METCR1673 Generic 2 minutes) tr=1.05 mm, 100% mlz=3271329 [M+H]

Molecular Weight:208.56
XLogP3:2.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:207.9902769
Monoisotopic Mass:207.9902769
Topological Polar Surface Area:17.1
Heavy Atom Count:13
Complexity:192
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes