4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Step 4: A suspension of C40 (3.2 g, 16.4 mM) in DCM (50 ml.) was treated with SOCIA solution of 2-benzylpyrrolidine (34.96 mg, 0.22 mmol) and 4-chloro-1H- pyrrolo[2, 3-b]pyridine-3-carbonitrile (P5) (35 mg, 0.20 mmol)was dissolved in NMP (0.5 ml) and was heated at 160 00 for 4 hours. The mixture was concentrated under reduced pressure and the residue purified by preparative HPLC (middle basic run) to give 4-(2- benzylpyrrolidin-1-yl)-1 H-pyrrolo[2, 3-b]pyridine-3-carbonitrile (El 07) (8 mg, 0.03 mmol, 12.8 % yield), LCMS ES 303.2 [M+H], Rt = 1.31 mins (Generic Basic Method).A solution of 2-benzylpiperidine (98.68 mg, 0.56 mmol) and 4-chloro-1H- pyrrolo[2, 3-b]pyridine-3-carbonitrile (P5) (50 mg, 0.28 mmol) in NMP (0.5 ml) was heated at 220 00 for 1 hour. The mixture was loaded onto an SOX cartridge and eluted with 2N NH3 in methanol. The mixture was concentrated under reduced pressure before being purified by preparative HPLC (middle basic run) to give 4-(2-benzyl-1-piperidyl)-1H-pyrrolo[2, 3- b]pyridine-3-carbonitrile (E106) (1.5 mg, 0.005 mmol, 1.6% yield), LOMS ES 317.3 [M+H], Rt = 1.40 mins (Generic Basic Method).

Molecular Weight:177.59
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:177.0093748
Monoisotopic Mass:177.0093748
Topological Polar Surface Area:52.5
Heavy Atom Count:12
Complexity:222
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes