Sodium Hydroxide → 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acid

HRID 2410688Notes

Reaction equation

HRID 2410688 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]2[NH:11][C:12]3[C:17]([C:18]([O:20]C)=[O:19])=[CH:16][C:15]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[N:14][C:13]=3[C:8]2=[CH:7][CH:6]=1>O1CCCC1.CO>[CH3:3][O:4][C:5]1[N:10]=[C:9]2[NH:11][C:12]3[C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)=[N:14][C:13]=3[C:8]2=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66605458methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate

Product 1

HCID 666053457-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acidYield 96.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide (1.0 N, 0.66 mL, 0.66 mmol) was added to a solution of methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (80 mg, 0.22 mmol) in a mixture of tetrahydrofuran (3 mL) and methanol (1 mL). After 1 hr, the organic solvents were removed on the rotary evaporator. The residue was diluted with water to bring most of the solid into solution and sufficient 1.0 N aqueous HCl was added to bring the pH of the mixture to about 3. After stirring for 0.5 hr, the precipitate was collected, washed with water, and dried under vacuum over solid sodium hydroxide to give 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acid (74 mg, 0.212 mmol, 96% yield) as an orange solid. MS (ESI) m/z 350.2 (M+H). 1H NMR (DMSO-d6) δ ppm 8.52 (1H, d, J=8.54 Hz), 8.17 (1H, s), 8.09 (2H, d, J=8.85 Hz), 7.07 (2H, d, J=8.85 Hz), 6.78 (1H, d, J=8.24 Hz), 4.02 (3H, s), 3.83 (3H, s).

Workup

  1. customthe organic solvents were removed on the rotary evaporator
  2. additionThe residue was diluted with water
  3. additionwas added
  4. customthe precipitate was collected
  5. washwashed with water
  6. dry with materialdried under vacuum over solid sodium hydroxide

Sources & evidence

ORD record
ord-8de630e3bd8546e2966aed2be1cac2cb
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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