Water → 2-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazole

HRID 1942641Notes

Reaction equation

HRID 1942641 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Br[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>COCCOC.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>[Cl:1][C:2]1[CH:3]=[C:4]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 584941012-(3-Chloro-4-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 584941402-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazoleYield 58.4%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (D69) (3 g), 2-bromo-1,3-thiazole (1.659 g) and Cs2CO3 (3.95 g) in 1,2-dimethoxyethane (DME) (40 mL)/water (10 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (661 mg) in one charge. The reaction vessel was sealed and heated under microwave at 120° C. for 2 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-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazole (D70) (1.5 g). MS (ES): C12H12ClNOS requires 253. found 254.1 (M+H+).

Workup

  1. additioncharge
  2. customThe reaction vessel was sealed
  3. temperatureheated under microwave at 120° C. for 2 h
  4. temperatureAfter cooling
  5. customthe reaction
  6. filtrationthe reaction mixture was filtered
  7. customthe filtrate was partitioned between ethyl acetate (150 mL) and saturated brine (50 mL)
  8. dry with materialThe organic phase was dried over sodium sulphate
  9. customevaporated in vacuo
  10. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-efb2454fa1a8478ab4cfe6942cae6185
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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