Potassium Carbonate → HCID 67026909, compound

HRID 1908765Notes

Reaction equation

HRID 1908765 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10](Cl)=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].B1(C=C)OB([CH:22]=[CH2:23])OB(C=C)O1.C1C=CN=CC=1.C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(OCC)C.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:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([CH:22]=[CH2:23])=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 10933837HCID 10933837, compound

Product 1

HCID 67026909HCID 67026909, compoundYield 83.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5,6-dichloronicotinic acid tert.-butyl ester (5.00 g, 20.0 mmol), and 2,4,6-trivinylcyclotriboroxane pyridine complex (9.700 mg, 40 mmol) in dioxane (30 mL), a solution of 2 M aq. K2CO3 (6 mL) followed by Pd(PPh3)4 (620 mg, 0.38 mmol) and triphenylphosphine (620 mg, 3.8 mmol) is added. The mixture is stirred at 100° C. for 2 h, cooled to rt and diluted with diethyl ether (200 mL). The mixture is extracted with 1M aq. NaOH (2×50 mL) and brine (50 mL). The org. phase is dried (Na2SO4), filtered and evaporated. The residue is purified by FC (SiO2, EA-heptane) to give 5-chloro-6-vinyl-nicotinic acid tert.-butyl ester (4.0 g) as a yellow oil; LC-MS: tR=1.05 min, [M+1+CH3CN]+=281.36.

Workup

  1. additionis added
  2. temperaturecooled to rt
  3. extractionThe mixture is extracted with 1M aq. NaOH (2×50 mL) and brine (50 mL)
  4. dry with materialphase is dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by FC (SiO2, EA-heptane)

Sources & evidence

ORD record
ord-d4a00a91f42d4c75a70325967a08a2b5
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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