Potassium Carbonate → 2-(2-Methyl-thiazol-4-yl)-benzaldehyde

HRID 1966680Notes

Reaction equation

HRID 1966680 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][C:11]1[S:12][CH:13]=[C:14](B2OC(C)(C)C(C)(C)O2)[N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][C:11]1[S:12][CH:13]=[C:14]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[N:15]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 811292-BromobenzaldehydeHCID 457863152-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

Product 1

HCID 585420382-(2-Methyl-thiazol-4-yl)-benzaldehydeYield 53%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-bromobenzaldehyde (0.063 mL, 0.54 mmol) in DMF (5 mL) and H2O (1 mL) are added 2-methylthiazole-4-boronic acid pinacol ester (122 mg, 0.54 mmol), Pd(PPh3)4 (63 mg, 0.054 mmol) and K2CO3 (112 mg, 0.81 mmol) at room temperature. The solution is heated to 120° C. for 1 hour in a microwave reactor. The reaction is cooled down and 3-mercaptopropyl-functionalized silica gel (500 mg) is added. The solution is stirred for 15 minutes and is filtered. The filtrate is washed with H2O (10 mL) and is extracted with EtOAc (3×15 mL). The combined organic layer is dried (MgSO4), filtered and concentrated. The residue is purified by silica gel flash chromatography eluting with 50% EtOAc in heptane to afford 2-(2-methyl-thiazol-4-yl)-benzaldehyde (58 mg, 53%) as a white foam.

Workup

  1. temperatureThe reaction is cooled down
  2. addition3-mercaptopropyl-functionalized silica gel (500 mg) is added
  3. filtrationis filtered
  4. washThe filtrate is washed with H2O (10 mL)
  5. extractionis extracted with EtOAc (3×15 mL)
  6. dry with materialThe combined organic layer is dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel flash chromatography
  10. washeluting with 50% EtOAc in heptane

Sources & evidence

ORD record
ord-95fcb2eded574bc7a8c2258259dfc628
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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