Methanol → HCID 71150146, compound

HRID 1482741Notes

Reaction equation

HRID 1482741 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+].CO>C(Cl)Cl.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>[O:21]=[C:18]1[NH:8][CH:7]=[C:6]([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:5]=[CH:4]1

Participants

6

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 71150146HCID 71150146, compoundYield 117.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

IMS (600 mL) and water (250 mL) were degassed thoroughly. tert-Butyl 4-bromophenethylcarbamate (32.7 g, 109 mmol), sodium carbonate (46.2 g, 436 mmol), palladium tetrakis (12.6 g, 11.0 mmol) and 2-methoxypyridine boronoic acid (25.0 g, 163 mmol) were added and the reaction mixture heated to 90° C. for 18 hours. The reaction was cooled to room temperature, filtered and the residue washed with IMS (100 mL) and ethyl acetate (1 L). The filtrate was washed with water (500 mL), dried (MgSO4) and concentrated to give a brown solid. The crude residue was subject to column chromatography (0 to 1.5% MeOH in DCM) to give a white solid, tert-butyl 4-(6-oxo-1,6-dihydropyridin-3-yl)phenethylcarbamate (20.95 g, 63.8 mmol, 58% yield).

Workup

  1. customIMS (600 mL) and water (250 mL) were degassed thoroughly
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washthe residue washed with IMS (100 mL) and ethyl acetate (1 L)
  5. washThe filtrate was washed with water (500 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a brown solid

Sources & evidence

ORD record
ord-155152fc6d9d4d078c3294344c8c8e7b
Source dataset
uspto-grants-2016_08
Patent number
US09415045B2

Reaction notes

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