2-(Triethylstannyl)oxazole → Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-oxazol-2-yl)benzoate

HRID 14293Notes

Reaction equation

HRID 14293 reaction equation
C([Sn](CC)(CC)[C:4]1[O:5][CH:6]=[CH:7][N:8]=1)C.[CH2:13]([N:16]([CH2:30][CH2:31][CH3:32])[C:17]([C:19]1[CH:20]=[C:21]([CH:26]=[C:27](I)[CH:28]=1)[C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH2:14][CH3:15]>CN(C)C=O>[CH2:30]([N:16]([CH2:13][CH2:14][CH3:15])[C:17]([C:19]1[CH:20]=[C:21]([CH:26]=[C:27]([C:4]2[O:5][CH:6]=[CH:7][N:8]=2)[CH:28]=1)[C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 149317842-(Triethylstannyl)oxazoleHCID 21086179Methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate

Product 1

HCID 21939658Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-oxazol-2-yl)benzoateYield 27.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 2-triethylstannyloxazole (Chem. Mater. 1994, 6, 1023) (1.5 g, 5.5 mmol) and methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate (1.8 g, 4.6 mmol) in dimethylformamide (12 mL) was degassed under reduced pressure for 15 min and purged with argon. Palladium(0)tetrakis(triphenylphosphine) (158 mg, 0.14 mmol) was added and the reaction mixture was degassed under reduced pressure for 15 min and then purged with argon. The reaction mixture was heated at reflux for 2 d, cooled to room temperature, diluted with ethyl acetate, washed with water (3×50 mL), dried (sodium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes) provided methyl 3-[(dipropylamino)carbonyl]-5-(1,3-oxazol-2-yl)benzoate (423 mg): 1H NMR (300 MHz, CDCl3) δ 8.73 (s, 1H), 8.23 (s, 1H), 8.11 (s, 1H), 7.76 (s, 1H), 7.28 (s, 1H), 3.97 (s, 3H), 3.49 (br s, 2H), 3.18 (br s, 2H), 1.72 (d, J=7 Hz, 2H), 1.55 (d, J=7 Hz, 2H), 1.00 (t, J=7 Hz, 3H), 0.75 (t, J=7 Hz, 3H).

Workup

  1. custompurged with argon
  2. customthe reaction mixture was degassed under reduced pressure for 15 min
  3. custompurged with argon
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 2 d
  6. additiondiluted with ethyl acetate
  7. washwashed with water (3×50 mL)
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-173312e7cda5466a9bf2bc08a7c25219
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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