Potassium Carbonate → HCID 68052599, compound

HRID 1685131Notes

Reaction equation

HRID 1685131 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[C:11]([C:23]([O-:25])=[O:24])[N:10]([CH3:26])[N:9]=2)=[CH:4][CH:3]=1.B1([C:36]2[CH:41]=[CH:40][C:39]([C:42]([NH:44][CH3:45])=[O:43])=[N:38][CH:37]=2)OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+].O.[OH-].[Li+]>C(O)C.[Pd].O>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:36]4[CH:37]=[N:38][C:39]([C:42](=[O:43])[NH:44][CH3:45])=[CH:40][CH:41]=4)=[CH:3][CH:4]=3)=[N:9][N:10]([CH3:26])[C:11]=2[C:23]([OH:25])=[O:24])=[CH:16][CH:17]=1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 168937Lithium hydroxide, monohydrateHCID 44119560N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamideHCID 86651931HCID 86651931, compoundHCID 178435160HCID 178435160, compound

Product 1

HCID 68052599HCID 68052599, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 3-(4-bromophenyl)-4-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-5-carboxylate T-12 (400 mg, 0.96 mmol) in ethanol (10 mL) and water (1 mL) were added 2-(N-methylamidocarboxy)-5-pyridineboronic acid pinacol ester (254 mg, 0.97 mmol), potassium carbonate (138 mg, 1.0 mmol) and polyethylene supported palladium catalyst (FibreCat FC 1007, 3% Pd, 300 mg). The reaction mixture was heated in a microwave reactor at 115° C. for 15 minutes. To the reaction mixture was added lithium hydroxide monohydrate (127 mg, 3.0 mmol). The reaction mixture was heated in a microwave reactor at 115° C. for 20 minutes. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The crude product was purified by RP-HPLC to afford the desired 4-(4-methoxybenzyloxy)-1-methyl-3-(4-(6-(methylcarbamoyl)pyridin-3-yl)phenyl)-1H-pyrazole-5-carboxylic acid T-13 (304 mg, 0.64 mmol).

Workup

  1. temperatureThe reaction mixture was heated in a microwave reactor at 115° C. for 20 minutes
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-8251f566e2ec4a5ab993e516f12810cb
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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