Cesium carbonate → HCID 67026987, compound

HRID 1908766Notes

Reaction equation

HRID 1908766 reaction equation
[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:12]=[C:11](Cl)[C:10]([CH:14]=[CH2:15])=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[C:23](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:24].B1(C=C)OB(C=C)OB(C=C)O1.C1C=CN=CC=1>O1CCOCC1>[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:12]=[C:11]([CH:23]=[CH2:24])[C:10]([CH:14]=[CH2:15])=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 67026909HCID 67026909, compound

Product 1

HCID 67026987HCID 67026987, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-6-vinyl-nicotinic acid tert.-butyl ester (2.0 g), Cs2CO3 (3.4 g), tri(tert.-butyl)phosphine (0.04 eq.), tris(dibenzylidenacetone)dipalladium (0.02 eq.), and 2,4,6-trivinylcyclotriboroxane pyridine complex (2.0 g) in dioxane (30 mL) is degassed and heated at 100° C. for 15 h. The mixture is 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 5,6-divinyl-nicotinic acid tert.-butyl ester (0.89 g) as an oil. LC-MS: tR=1.01 min, [M+1]+=232.04.

Workup

  1. customis degassed
  2. temperatureThe mixture is cooled to rt
  3. additiondiluted with diethyl ether (200 mL)
  4. extractionThe mixture is extracted with 1M aq. NaOH (2×50 mL) and brine (50 mL)
  5. dry with materialphase is dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by FC (SiO2, EA-heptane)

Sources & evidence

ORD record
ord-5566e524c1f9474db24fb4aa88800423
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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