Potassium Carbonate → 4-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

HRID 530756Notes

Reaction equation

HRID 530756 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=1.[CH3:19][C:20]1[N:21]=[C:22]([Sn](CCCC)(CCCC)CCCC)[S:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=[C:2]([C:22]2[S:23][CH:24]=[C:20]([CH3:19])[N:21]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 164271304-Methyl-2-(tributylstannyl)-1,3-thiazoleHCID 866691142-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

Product 1

HCID 681599974-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of compound 21 (4.17 mmol) in DMF (15 mL) were added 4-methyl-2-(tributylstannyl)thiazole (5 mmol), dichlorobis(triphenylphosphine) palladium (II) chloride (0.417 mmol), and K2CO3 (5 mmol). The reaction mixture was stirred at 110° C. under microwave irradiations for 1 hr. The solution was concentrated in vacuo and H2O and DCM were added. The layers were separated and the organic layer was concentrated. The crude was purified by silica gel chromatography (eluent: DCM) to give compound 22 in quantitative yield. MS (ESI, EI+): m/z=357.87 (MH+).

Workup

  1. concentrationThe solution was concentrated in vacuo and H2O and DCM
  2. additionwere added
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated
  5. customThe crude was purified by silica gel chromatography (eluent: DCM)

Sources & evidence

ORD record
ord-c1d5bf4eb9464ffeb9bf13fd7ee9b79f
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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