Cesium carbonate → Methyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)propanoate

HRID 2046936Notes

Reaction equation

HRID 2046936 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[CH3:15][O:16][C:17](=[O:22])[C:18](Br)([CH3:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:15][O:16][C:17](=[O:22])[C:18]([CH3:20])([N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 59599416Methyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (5.0 g, 0.026 mol), 2-bromo-2-methylpropionic acid methyl ester (3.50 mL, 0.0270 mol), Cs2CO3 (12 g, 39 mmol) in DMF (200 mL) was heated at 90° C. overnight. Reaction mixture was concentrated in vacuo, water was added, and the mixture was extracted with EtOAc (3×50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the title compound as a light yellow solid. MS (ES+): m/z 295.13, 296.16 (100, 50) [MH+]. HPLC: tR=3.35 min (ZQ3 polar—5 min).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo, water
  3. additionwas added
  4. extractionthe mixture was extracted with EtOAc (3×50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16640dc0584f434bb11c867acf9f2c27
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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