Cesium carbonate → HCID 59187446, compound

HRID 1944501Notes

Reaction equation

HRID 1944501 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH3:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[S:11][C:10]([CH3:9])=[N:14][CH:13]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 119931-Chloro-2-iodobenzeneHCID 771292-Methylthiazole

Product 1

HCID 59187446HCID 59187446, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

1-chloro-2-iodobenzene (500 μL, 4.1 mmol) is dissolved in DMF (10 mL), then 2-methylthiazole (406 mg, 4.1 mmol), triphenylphosphine (54 mg, 0.20 mmol), cesium carbonate (1.33 g, 4.1 mmol), palladium(II) acetate (92 mg, 0.41 mmol) are added and the mixture is stirred at 140° C. for 24 h. The reaction mixture is diluted with 1 M HCl (10 mL) and extracted into EtOAc (3×10 mL). The organic layers are combined and washed with H2O (2×20 mL) and brine (10 mL), then dried (MgSO4), filtered, concentrated and purified by silica gel chromatography (EtOAc/hexane, gradient) to give 5-(2-chlorophenyl)-2-methylthiazole 6. 1H-NMR (400 MHz, CDCl3) δ=7.80 (s, 1H), 7.48 (m, 2H), 7.28 (m, 2H), 2.75 (s, 3H). MS calcd. for C10H9ClNS (M+H+) 210.0. found 210.1.

Workup

  1. extractionextracted into EtOAc (3×10 mL)
  2. washwashed with H2O (2×20 mL) and brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (EtOAc/hexane, gradient)

Sources & evidence

ORD record
ord-83098ff672b140ff84dbee869d6673c0
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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