Cesium carbonate → 2-[4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 1942638Notes

Reaction equation

HRID 1942638 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=2)O1.Br[C:25]1[S:26][CH:27]=[CH:28][N:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O.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].C(Cl)Cl>[CH3:18][CH:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[CH:10][C:11]=1[C:19]([F:20])([F:21])[F:22])[CH3:17]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 58494057HCID 58494057, compound

Product 1

HCID 669822262-[4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazoleYield 52.4%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4,4,5,5-tetramethyl-2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane (D42) (160 mg), 2-bromo-1,3-thiazole (119 mg) and cesium carbonate (237 mg) in acetonitrile (15 mL) and water (3.75 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (39.6 mg) in one charge. The reaction vessel was sealed and heated under microwave at 120° C. for 1 h. After cooling the reaction, the reaction mixture was filtered and the filtrate was partitioned between ethyl acetate (150 mL) and saturated brine (50 mL). The organic phase was dried over sodium sulphate and evaporated in vacuo. The crude product was purified by column chromatography to give 2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole (D66) (73 mg). MS (ES): C13H12F3NOS requires 287. found 288.1 (M+H+).

Workup

  1. additioncharge
  2. customThe reaction vessel was sealed
  3. temperatureAfter cooling
  4. customthe reaction
  5. filtrationthe reaction mixture was filtered
  6. customthe filtrate was partitioned between ethyl acetate (150 mL) and saturated brine (50 mL)
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. customevaporated in vacuo
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-1f070925888b4a18a0544574ccb23e57
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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