Cesium fluoride → 5-(4-Chloro-6-methylpyridin-2-yl)thiazole

HRID 523154Notes

Reaction equation

HRID 523154 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.C([Sn](CCCC)(CCCC)[C:15]1[S:19][CH:18]=[N:17][CH:16]=1)CCC.[F-].[Cs+]>[Cu]I.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>[Cl:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([C:15]2[S:19][CH:18]=[N:17][CH:16]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27632575-(Tributylstannyl)-1,3-thiazoleHCID 119590832,4-Dichloro-6-methylpyridine

Product 1

HCID 901180015-(4-Chloro-6-methylpyridin-2-yl)thiazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-methylpyridine (29 mg, 0.18 mmol), 5-(tributylstannyl)thiazole (66 mg, 0.18 mmol), CuI (8 mg, 0.04 mmol), CsF (81 mg, 0.53 mmol), and Pd(PPh3)4 (10 mg, 8.9 μmol). The vial was capped with a septum screw-cap and then placed under N2 atmosphere. To the vial was added degassed DMF (1 mL). The vial was placed in a 80° C. heating block with stirring for 1 hour. The mixture was allowed to cool to room temperature and was then directly purified via C18 chromatography (water:MeOH w/0.1% TFA) to afford 5-(4-chloro-6-methylpyridin-2-yl)thiazole as a white solid. MS: MS m/z 211.1 (M++1). This material was directly carried forward into step 2.

Workup

  1. customTo a 2 dram vial equipped with a stir bar
  2. customThe vial was capped with a septum
  3. customscrew-cap
  4. additionTo the vial was added
  5. customdegassed DMF (1 mL)
  6. customwas placed in a 80° C.
  7. temperatureheating block
  8. customwas then directly purified via C18 chromatography (water:MeOH w/0.1% TFA)

Sources & evidence

ORD record
ord-3969fdb229da4887beaeb1845240248e
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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