Water → HCID 59855814, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1-(4-fluorobenzyl)-3-[(2-methoxyethoxy)methyl]-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (542 mg 1.4645 mmol) in THF (10 mL) was added lithium hydroxide monohydrate (123 mg 2.929 mmol, 2 eq.) and water (5 mL) and the clear solution was warmed to 40° C. for 3 hours. THF was removed under vacuum and 1 M HCl added (2.93 mL 2.93 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 400 mg (76%). LC-MS (Eclipse XDB-C8, 0.8 mL/min, gradient 80:20 to 5:95H2O (+0.1% HOAc):CH3CN—5 minutes, ESI, +mode): RT—1.753 min, m/e=359.1 (M+H+, base). 1H-NMR (300 MHz, CD3OD): δ=3.68 (s, 3H), 3.60 (m, 2H), 3.73 (m, 2H), 4.86 (s, 2H), 5.64 (s, 2H), 7.12 (m, 2H), 7.36 (m, 2H), 8.06 (s, 1H), 8.3 (s, 1H), 8.86 (s, 1H).

Provenance & Evidence