Sodium Carbonate → 2-Methoxy-5-(thiazol-4-yl)benzaldehyde

HRID 1289988Notes

Reaction equation

HRID 1289988 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])=[O:2].Br[C:15]1[N:16]=[CH:17][S:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C(OCC)(=O)C.COCCOC>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:15]2[N:16]=[CH:17][S:18][CH:19]=2)=[CH:4][C:3]=1[CH:1]=[O:2]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2759225(3-Formyl-4-methoxyphenyl)boronic acidHCID 27632184-Bromothiazole

Product 1

HCID 189224822-Methoxy-5-(thiazol-4-yl)benzaldehydeYield 55%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

(3-Formyl-4-methoxyphenyl)boronic acid (309 mg, 1.71 mmol), 4-bromothiazole (250 mg, 1.52 mmol, prepared as described by J. Trybulski and H. J. Brabander, U.S. Pat. No. 4,990,520, 1991), and tetrakis(triphenylphosphine)palladium(0) (88 mg, 0.076 mmol) were added to a mixture of water (3.5 mL), ethylene glycol dimethyl ether (3.5 mL), and sodium carbonate (805 mg, 7.6 mmol). The mixture was heated in an oil bath at 80° C. for 3 h, allowed to cool to 25° C., and partioned between ethyl acetate (40 mL) and water (20 mL). The aqueous layer was extracted with 2×40 mL of dichioromethane and the combined organic layers dried (sodium sulfate), decanted, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with 10% ethyl acetate in hexane to give 182 mg (55% yield) of the title compound as a white solid. NMR (400 MHz, CDCl3): δ 10.51 (s, 1H), 8.88 (d, 1H, J=2 Hz), 8.32 (d, 1H, J=2 Hz), 8.24 (dd, 1H, J=9,2 Hz), 7.54 (d, 1H, J=2 Hz), 7.09 (d, 1H, J=9 Hz), 3.99 (s, 3H). Mass spectrum (NH3 /CI): 220 (M+1).

Workup

  1. temperatureto cool to 25° C.
  2. extractionThe aqueous layer was extracted with 2×40 mL of dichioromethane
  3. dry with materialthe combined organic layers dried (sodium sulfate)
  4. customdecanted
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-218669f5a8814099b22fb1328ad15d1f
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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