Sodium Carbonate → HCID 58002252, compound

HRID 1642801Notes

Reaction equation

HRID 1642801 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][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.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][O:14][C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 58002252HCID 58002252, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
85 °C

Procedure

22.26 g (96.78 mmol) of ethyl 5-bromonicotinate, 25.00 g (164.5 mmol) of 4-methoxyphenylboronic acid, 0.56 g (0.48 mmol) of tetrakis(triphenylphosphine)palladium(0) and 20.51 g (193.6 mmol) of sodium carbonate were dissolved in a mixture of 180 ml of 1,2-dimethoxyethane, 50 ml of water and 400 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 flash chromatography (dichloromethane/acetonitrile 100:2<100:5). Yield: 20.18 g (72% 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 flash chromatography (dichloromethane/acetonitrile 100:2<100:5)

Sources & evidence

ORD record
ord-cea8f43fd16a4d8eb65385bc54d3a58f
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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