Sodium Hydroxide → HCID 71611733, compound

HRID 1527959Notes

Reaction equation

HRID 1527959 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:7]=1)=[O:5])C.[OH-].[Na+]>CO.C1COCC1.O>[Br:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][CH:22]2[CH2:25][CH2:24][CH2:23]2)=[C:13]([CH:18]=1)[CH2:12][N:8]1[C:9]([CH3:11])=[CH:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86688732HCID 86688732, compound2×

Product 1

HCID 71611733HCID 71611733, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of -(5-bromo-2-cyclobutylmethoxy-benzyl)-5-methyl-1h-pyrazole-3-carboxylic acid ethyl ester, 24 (0.12 g, 0.29 mmol) in a mixture of MeOH (2 mL) and THF (4 ml) was added a solution of NaOH (0.061 g, 1.45 mmol) in 2 ml of H2O. The resulting mixture was heated at 100° C. in an Emrys microwave reactor for 20 minutes. The mixture was poured into water (20 mL) and extracted with EtOAc (3×15 mL). The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles were removed in vacuum to yield 1-(5-bromo-2-cyclobutylmethoxy-benzyl)-5-methyl-1h-pyrazole-3-carboxylic acid, 25

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customthe volatiles were removed in vacuum

Sources & evidence

ORD record
ord-945811ae738b42cb8ffb54ae846eeb9d
Source dataset
uspto-grants-2015_07
Patent number
US09090566B2

Reaction notes

Loading…