Water → HCID 59855807, compound

HRID 2377117Notes

Reaction equation

HRID 2377117 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][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][CH3:22])=[CH:8]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].O>CO>[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][CH3:22])=[CH:8]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59855852HCID 59855852, compound

Product 1

HCID 59855807HCID 59855807, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 1-(4-fluorobenzyl)-3-(methoxymethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate. (960 mg 1.2.924 mmol) in methanol (10 mL) was added lithium hydroxide monohydrate (246 mg 5.847 mmol, 2 eq.) and water (5 mL), and the clear solution was warmed to 40° C. for 15 hours. Methanol was removed under vacuum and 1 M HCl added (5.8 mL 5.847 mmol, 2 eq.). The crude product precipitated and was filtered under vacuum, washed with ether (40 ml) and dried in vacuo at 75° C. to give the title product as a white powder 664 mg (72%). LC-MS (Eclipse XDB-C8, 0.8 mL/min, gradient 80:20 to 5:95H2O (+0.1% HOAc):CH3CN—3 minutes, ESI, +mode): RT-0.828 min, m/e=315.2 (M+H+, base). 1H-NMR (300 MHz, DMSO): δ=3.28 (s, 3H), 4.64 (s, 2H), 5.62 (s, 2H), 7.20 (t, 2H), 7.38 (m, 2H), 7.94 (s, 1H), 8.36 (s, 1H), 8.97 (s, 1H).

Workup

  1. customMethanol was removed under vacuum and 1 M HCl
  2. additionadded (5.8 mL 5.847 mmol, 2 eq.)
  3. customThe crude product precipitated
  4. filtrationwas filtered under vacuum
  5. washwashed with ether (40 ml)
  6. customdried in vacuo at 75° C.

Sources & evidence

ORD record
ord-fe70a7456c7841239645984a0b2fa314
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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