Cesium carbonate → HCID 22180765, compound

HRID 1796078Notes

Reaction equation

HRID 1796078 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.CC1(C)COB([C:16]2[CH:17]=[N:18][S:19][CH:20]=2)OC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:16]2[CH:17]=[N:18][S:19][CH:20]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 122742,6-DibromopyridineHCID 22180767HCID 22180767, compound

Product 1

HCID 22180765HCID 22180765, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A degassed solution of 2,6-dibromopyridine (0.86 g, 3.56 mmol) and 4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)isothiazole (0.35 g, 1.78 mmol) in dry 1,4-dioxane (10 ml) was stirred under an atmosphere of nitrogen, then cesium carbonate (1.20 g, 3.68 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.10 g, 5 mol %) added. This mixture was heated to reflux for 18 h. After cooling to ambient temperature, solvent was removed in vacuo, the residue dissolved in dichloromethane, washed with water and saturated brine, then dried over magnesium sulfate, filtered and evaporated in vacuo to give a solid. Purification by chromatography on silica gel, eluting with dichloromethane on a gradient of methanol (0-5%), gave 2-bromo-6-(isothiazol-4-yl)pyridine (0.33 g) as a white solid: δH (400 MHz, CDCl3) 7.42 (1H, dd, J 7 and 2), 7.60 (2H, m), 9.01 (1H, s), 9.16 (1H, s); m/z (ES+) 240/242 (M++H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 18 h
  3. customsolvent was removed in vacuo
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give a solid
  10. customPurification by chromatography on silica gel
  11. washeluting with dichloromethane on a gradient of methanol (0-5%)

Sources & evidence

ORD record
ord-a0a622d06a7a4f0692968fa1b1a1b600
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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