4H-Pyrrolo[3,2-c]pyridin-4-one, 1,5,6,7-tetrahydro-2-iodo- synthesis

Yield:1609679-06-2 89%

Reaction Conditions:

with N-iodo-succinimide in tetrahydrofuran;methanol at -70; for 1.5 h;

Steps:

1.1 Step 1. 2-lodo-1 ,5,6, 7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

To a solution of 1 ,5,6,7 -tetrahydro-pyrrolo[3,2-c]pyridin-4-one (0.12 g, 0.85 mmol) in dry THF (5 ml) and MeOH (1.5ml), kept at -70 oc, N-iodosuccinimide (0.19 g, 0.84 mmol) was added. After 1.5 h the reaction was quenched with a5 saturated solution of Na2S205, let to reach r.t. and the solvent was removed under reduced pressure. The residuewas suspended in water and the white solid was filtered and rinsed with water (0.16 g), while the filtrate wasextracted with DCM (3 x 10 ml). The organic layer was dried over anhydrous Na2S04, filtered and concentratedaffording a second aliquot of product (32 mg, 89% total yield).1H NMR (600 MHz, DMSO-dG) o ppm 2.72 (t, J=6.87 Hz, 2 H) 3.30 - 3.32 (m, 2 H) 6.34 (s, 1 H) 6.90 (br. s., 1 H)10 11.61 (br. s., 1 H).

References:

WO2014/72220,2014,A1 Location in patent:Page/Page column 75