Sodium Carbonate → HCID 71150146, compound

HRID 1853449Notes

Reaction equation

HRID 1853449 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[C:18](=[O:21])([O-])[O-].[Na+].[Na+].[CH2:24]([N:31]1C=C(B2OC(C)(C)C(C)(C)O2)C=N1)[C:25]1C=CC=[CH:27][CH:26]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.CCCCCCC>[O:21]=[C:18]1[NH:31][CH:24]=[C:25]([C:2]2[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=2)[CH:26]=[CH:27]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 71150146HCID 71150146, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
90 °C

Procedure

IMS (50 mL) and water (16 mL) were degassed thoroughly. tert-Butyl 4-bromophenethylcarbamate (3.52 g, 11.7 mmol), sodium carbonate (5.0 g, 46.9 mmol), palladium tetrakis (1.35 g, 1.2 mmol) and 1-benzyl-1H-pyrazole-4-boronic acid pinacol ester (5.0 g, 17.6 mmol) were added and the reaction mixture heated to 90° C. overnight. The reaction was partitioned between ethyl acetate (500 mL) and water (250 mL) and brine (250 mL), then dried (MgSO4). Filtration and removal of the solvent gave the crude residue which was subject to column chromatography (50% ethyl acetate/heptane) to give tert-butyl 4-(6-oxo-1,6-dihydropyridin-3-yl)phenethylcarbamate (4.2 g, 11.1 mmol, 95% yield).

Workup

  1. customIMS (50 mL) and water (16 mL) were degassed thoroughly
  2. customThe reaction was partitioned between ethyl acetate (500 mL) and water (250 mL) and brine (250 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and removal of the solvent
  5. customgave the crude residue which

Sources & evidence

ORD record
ord-b75ba6b5f8d34b6881a2a1436f00c786
Source dataset
uspto-grants-2015_02
Patent number
US08962646B2

Reaction notes

Loading…