Sodium Carbonate → Methyl 4-pyridin-3-ylbenzoate

HRID 1677132Notes

Reaction equation

HRID 1677132 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=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(Cl)Cl.O.CCO.COCCOC>[CH3:18][O:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:12][CH:13]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 12081Methyl 4-bromobenzoateHCID 27343783-Pyridinylboronic acid

Product 1

HCID 4133187Methyl 4-pyridin-3-ylbenzoateYield 50%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

Procedure H′: 750 mg of pyridine-3-boronic acid (6.14 mmol), 1.34 g of methyl 4-bromobenzoate (6.22 mmol) are put in the reaction vessel with 25 ml of DME:water:EtOH=7:3:2.). 6.25 ml of aqueous 2M Na2CO3 is added to the mixture and 250 mg of tetrakis(triphenylphosphine is added. The vessel is sealed and heated at 110° C. for 40 min in Microwave machine (MARS). After cooling, water and CH2Cl2 are added. The CH2Cl2 layer is separated, washed by brine, dried over Na2SO4 and evaporated. The crude product is applied to silica-gel column chromatography (Hexane:AcOEt=3:1) to give 4-pyridin-3-yl-benzoic methyl ester. Yield 50%: mass spectrum (m/e): 214 (M+1); 1H-NMR (CDCl3): 8.92 (m, 1H), 8.68 (m, 1H), 8.18 (d, 2H, J=7.6 Hz), 7.95 (m, 1H), 7.69 (d, 2H, J=7.6 Hz), 7.43 (m, 1H), 3.99 (s, 3H).

Workup

  1. additionis added
  2. customThe vessel is sealed
  3. temperatureAfter cooling
  4. customThe CH2Cl2 layer is separated
  5. washwashed by brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-4c6bc280929e4b18a9a60a5c912cb209
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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