Sodium Carbonate → Ethyl 5-[4-(1-methylethyl)phenyl]pyridine-3-carboxylate

HRID 1642788Notes

Reaction equation

HRID 1642788 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:13][CH:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.CN(C)C=O.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>[CH3:13][CH:14]([C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=[N:4][CH:3]=2)=[CH:18][CH:17]=1)[CH3:15]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 27734804-Isopropylphenylboronic acid

Product 1

HCID 58002314Ethyl 5-[4-(1-methylethyl)phenyl]pyridine-3-carboxylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

4.68 g (20.32 mmol) of ethyl 5-bromonicotinate, 5.00 g (30.49 mmol) of 4-(1-methylethyl)-phenylboronic acid, 0.12 g (0.10 mmol) of tetrakis(triphenylphosphine)palladium(0) and 4.31 g (40.65 mmol) of sodium carbonate were dissolved in a mixture of 37 ml of 1,2-dimethoxyethane, 10.5 ml of water and 84 ml of dimethylformamide and stirred at 85° C. for 18 h. For work-up, some of the dimethylformamide was removed under reduced pressure, and the reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was dried over sodium sulphate and the crude product was purified by preparative HPLC. Yield: 2.42 g (44% of theory)

Workup

  1. customFor work-up, some of the dimethylformamide was removed under reduced pressure
  2. additionthe reaction mixture was diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-045c5b80d70f4e10b487447845c1de2b
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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