Water → 2-(1-Methylethoxy)-5-(2-thiazolyl)benzonitrile

HRID 1942636Notes

Reaction equation

HRID 1942636 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].Br[C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C.C(OCC)(=O)C.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>[CH3:3][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:1]

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 575060272-Isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 575060282-(1-Methylethoxy)-5-(2-thiazolyl)benzonitrileYield 53.9%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 2-[(1-methylethyl)oxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (D39) (109 mg), 2-bromo-1,3-thiazole (93 mg) and cesium carbonate (148 mg) in acetonitrile (3 mL)/water (0.750 mL) stirred under nitrogen was added PdCl2(dppf)-CH2Cl2 adduct (31.0 mg). The reaction vessel was sealed and heated under microwave at 120° C. for 1 h. After cooling the reaction, the reaction mixture was diluted with ethyl acetate, filtered through celite. The filtrate was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulphate and evaporated in vacuo to give the crude product, which was purified by column chromatography to afford 2-[(1-methylethyl)oxy]-5-(1,3-thiazol-2-yl)benzonitrile (D64) (50 mg). MS (ES): C13H12N2OS requires 244. found 245.1 (M+H+).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe reaction
  4. filtrationfiltered through celite
  5. customThe filtrate was partitioned between ethyl acetate and water
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customevaporated in vacuo
  8. customto give the crude product, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e977d882c7644fb3b83bd450bb46b14b
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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