Water → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(2,4-difluorophenyl)methyl]-3-[(2-methoxyethoxy)methyl]-

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Reaction Conditions

Reaction Steps

To a solution of methyl 1-(2,4-difluorobenzyl)-3-[(2-methoxyethoxy)methyl]-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (2000 mg 5.123 mmol) in methanol (10 mL) was added lithium hydroxide monohydrate (430 mg 10.246 mmol, 2 eq.) and water (10 mL) and the clear solution was warmed to 40° C. for 3 hours. THF was removed under vacuum and 1 M HCl added (10.3 mL 10.3 mmol, 2 eq.). The crude product was extracted into EtOAc (3×30 mL), then DCM:MeOH 100:5 (3×30 mL). The organics were dried (Na2SO4), volatiles were removed in vacuo to give the title product as a cream colored powder 1563 mg (82%). LC-MS (Eclipse XDB-C8, 0.8 mL/min, gradient 80:20 to 5:95H2O (+0.1% HOAc):CH3CN—3 minutes, ESI, +mode): RT—0.91 min, m/e=377.2 (M+H+, base). 1H-NMR (300 MHz, DMSO): δ=3.42 (s, 3H), 3.46 (m, 2H), 3.60 (m, 2H), 4.69 (s, 2H), 5.66 (s, 2H), 7.07 (m, 1H), 7.36 (m, 2H), 7.82 (s, 1H), 8.36 (s, 1H), 8.98 (s, 1H).

Provenance & Evidence