Water → HCID 59855814, compound

HRID 2377102Notes

Reaction equation

[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([O:18]C)=[O:17])[CH:15]=[C:10]3[C:9]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:8]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([OH:18])=[O:17])[CH:15]=[C:10]3[C:9]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:8]2)=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

customTHF was removed under vacuum and 1 M HCl
additionadded (2.93 mL 2.93 mmol, 2 eq.) the crude product
extractionwas extracted into EtOAc (3×30 mL)
dry with materialThe organics were dried (Na2SO4) volatiles
customwere removed in vacuo

Sources & evidence

ORD record: ord-f3ac869c71fe4093875bd48914945ad5
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468375B2

Reaction notes

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