Potassium Carbonate → HCID 58541979, compound

HRID 1966688Notes

Reaction equation

HRID 1966688 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O)=[O:2].Br[C:15]1[S:16][C:17]([CH3:20])=[CH:18][N:19]=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][O:9][C:7]1[CH:6]=[CH:5][C:4]([C:15]2[S:16][C:17]([CH3:20])=[CH:18][N:19]=2)=[C:3]([CH:8]=1)[CH:1]=[O:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343652-Formyl-4-methoxybenzeneboronic acidHCID 219061062-Bromo-5-methyl-1,3-thiazole

Product 1

HCID 58541979HCID 58541979, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-formyl-4-methoxyphenylboronic acid (200 mg, 1.11 mmol) in DMF (10 mL) and H2O (2 mL) are added 2-bromo-5-methylthiazole (217 mg, 1.22 mmol), Pd(PPh3)4 (128 mg, 0.11 mmol) and K2CO3 (230 mg, 1.67 mmol) at room temperature. The solution is heated to 120° C. for 1 hour in a microwave reactor. The solution is cooled down and 3-mercaptopropyl-functionalized silica gel (500 mg) is added. The solution is stirred for 15 minutes and filtered. The filtrate is washed with H2O (15 mL) and is extracted with EtOAc (3×15 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash chromatography eluting with 50% EtOAc in heptane to afford 5-methoxy-2-(5-methyl-thiazol-2-yl)-benzaldehyde (160 mg, 63%) as a white foam.

Workup

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

Sources & evidence

ORD record
ord-a3117741e83d42c987191a6a53d8520e
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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