Potassium Carbonate → 1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2356356Notes

Reaction equation

HRID 2356356 reaction equation
[OH:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10]([OH:12])=O)[C:6](=[O:13])[N:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:22][C:23]1([CH3:37])[C:27]([CH3:29])([CH3:28])[O:26][B:25]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[O:24]1.C([O-])([O-])=O.[K+].[K+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)(Cl)Cl.C(Cl)Cl>[OH:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10]([NH:36][C:33]2[CH:32]=[CH:31][C:30]([B:25]3[O:26][C:27]([CH3:29])([CH3:28])[C:23]([CH3:37])([CH3:22])[O:24]3)=[CH:35][CH:34]=2)=[O:12])[C:6](=[O:13])[N:5]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 533934301-(2-Hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazole-4-carboxylic Acid

Product 1

HCID 593839381-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,3-dihydro-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A flask was charged with 1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (0.500 g, 1.72 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (0.377 g, 1.72 mmol), K2CO3 (0.476 g, 3.44 mmol), HATU (0.982 mg, 2.58 mmol) and CH2Cl2 (10 mL) and the mixture stirred at rt for 14 h. The mixture was diluted with CHCl3 (100 mL), washed with water and sat. NaHCO3. The organic layer was dried over Na2SO4, filtered and evaporated. The title compound was obtained as a white solid (873 mg). MS (ESI pos. ion) m/z: 492 (MH+). Calc'd exact mass for C27H34BN3O5: 491.

Workup

  1. washwashed with water and sat. NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8d12c2eb72b1405e8e74c335063b8b78
Source dataset
uspto-grants-2010_07
Patent number
US07759344B2

Reaction notes

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