Sodium Hydroxide → 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-chloro-2-thiophenecarboxylic acid

HRID 1845588Notes

Reaction equation

HRID 1845588 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Cl:9][C:10]1[S:14][C:13]([C:15]([O:17]C)=[O:16])=[CH:12][C:11]=1[C:19]1[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=1.[OH-].[Na+]>O1CCCC1>[Br:8][C:20]1[CH:21]=[N:22][N:23]([CH3:24])[C:19]=1[C:11]1[CH:12]=[C:13]([C:15]([OH:17])=[O:16])[S:14][C:10]=1[Cl:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 57826577Methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

Product 1

HCID 578264444-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-chloro-2-thiophenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

NBS (1.243 g, 6.98 mmol) was added in portions to a 150 mL sealed tube reactor containing methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (1.47 g, 5.73 mmol) [Prepared according to the procedure of Example 151] in Tetrahydrofuran (THF) (40 ml) at room temperature. The mixture was heated to 70° C. for 1 h. 6N NaOH (20 ml, 120 mmol) was then added and the mixture stirred at 70° C. for an additional 2 h. The mixture was partitioned between CHCl3 and H2O, the organic layer dried with Na2SO4 and concentrated affording the title compound which was used without further purification (385 mg, 1.4 mmol, 30%): LC-MS (ES) m/z=302 (M+H)+.

Workup

  1. customsealed tube reactor
  2. customPrepared
  3. customat room temperature
  4. customThe mixture was partitioned between CHCl3 and H2O
  5. dry with materialthe organic layer dried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c7ecd81557b04f399b389a094419898f
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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