Sodium Hydroxide → 1-methyl-5-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrole-3-carboxylic acid

HRID 1967117Notes

Reaction equation

HRID 1967117 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[N:11]([CH3:12])[N:10]=[CH:9][CH:8]=2)=[CH:5][C:4]([C:13]([O:15]C)=[O:14])=[CH:3]1.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]2[N:11]([CH3:12])[N:10]=[CH:9][CH:8]=2)=[CH:5][C:4]([C:13]([OH:15])=[O:14])=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58172926methyl 1-methyl-5-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 581729331-methyl-5-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrole-3-carboxylic acidYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 1-methyl-5-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrole-3-carboxylate (200 mg, 0.91 mmol) and sodium hydroxide (3.04 ml, 18.24 mmol) in tetrahydrofuran (4.561 ml) was stirred in a sealed tube for 12 h at 70° C. The reaction mixture was then partitioned between H2O-DCM and the pH of the aqueous phase was adjusted to ˜4 and washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and used directly without further purification yielding 1-methyl-5-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrole-3-carboxylic acid (187 mg, 0.87 mmol, 95% yield) as a white solid: LCMS (ES) m/e 206 (M+H)+.

Workup

  1. customThe reaction mixture was then partitioned between H2O-DCM
  2. washwashed several times with DCM
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. customused directly without further purification

Sources & evidence

ORD record
ord-f844a05285cd4a32bdb0956c652de7d7
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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