Dichloromethane → HCID 68285193, compound

HRID 1497666Notes

Reaction equation

HRID 1497666 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1.[N:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.O1CCOCC1>[N+:19]([C:15]1[CH:14]=[C:13]([C:3]2[N:4]=[C:5]([CH:7]3[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)[S:6][C:2]=2[C:25]2[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=1)([O-:21])=[O:20]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 68285300HCID 68285300, compound

Product 1

HCID 68285193HCID 68285193, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5-bromo-4-(3-nitrophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazole (140 mg, 0.379 mmol) was dissolved into a mixture of degassed dioxane (8 mL) and water (1.6 mL). 2-(4-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (78 mg, 0.379 mmol, 1 eq.), cesium carbonate (370 mg, 1.137 mmol, 3 eq.) and PdCl2(dppf)2.CH2Cl2 (31 mg, 0.0379 mmol, 0.1 eq) were subsequently added to the solution. The mixture so obtained was stirred and heated to reflux under argon atmosphere for 5 h. After cooling, the suspension was filtered through a celite pad, and evaporated to dryness. The crude was re-dissolved in ethyl acetate and washed twice with brine. The organic layer was dried over sodium sulphate and evaporated to dryness. The solid material so obtained was then purified by silica gel column chromatography eluting with ethyl acetate/Hex (6/4) yielding the title compound (98 mg, 70%).

Workup

  1. customThe mixture so obtained
  2. temperatureheated
  3. temperatureto reflux under argon atmosphere for 5 h
  4. temperatureAfter cooling
  5. filtrationthe suspension was filtered through a celite pad
  6. customevaporated to dryness
  7. dissolutionThe crude was re-dissolved in ethyl acetate
  8. washwashed twice with brine
  9. dry with materialThe organic layer was dried over sodium sulphate
  10. customevaporated to dryness
  11. customThe solid material so obtained
  12. customwas then purified by silica gel column chromatography
  13. washeluting with ethyl acetate/Hex (6/4)

Sources & evidence

ORD record
ord-1d07df3eb18d4c5f8261c6b24b648c3e
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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