Triethylamine → HCID 69079583, compound

HRID 244865Notes

Reaction equation

HRID 244865 reaction equation
[CH:1]([N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13])=[CH2:2].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:44]1[CH:45]=[CH:46][C:47]2[C:48]3[N:56]([CH2:57][C:58]([CH3:61])([OH:60])[CH3:59])[C:55]([CH2:62][CH3:63])=[N:54][C:49]=3[CH:50]=[N:51][C:52]=2[CH:53]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:62]([C:55]1[N:56]([CH2:57][C:58]([OH:60])([CH3:61])[CH3:59])[C:48]2[C:47]3[CH:46]=[CH:45][C:44]([CH:2]=[CH:1][N:3]4[C:7](=[O:8])[C:6]5[C:5](=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:4]4=[O:13])=[CH:53][C:52]=3[N:51]=[CH:50][C:49]=2[N:54]=1)[CH3:63]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 80271Tri-o-tolylphosphineHCID 219842201-(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Product 1

HCID 69079583HCID 69079583, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (64 mg, 0.29 mmol), acetonitrile (50 mL), N-vinylphthalimide (1.19 g, 6.89 mmol), triethylamine (2.4 mL, 17 mmol), tri-o-tolylphosphine (260 mg, 0.86 mmol) and 1-(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (2.00 g, 5.74 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120° C. in an oil bath for 16 hours. The reaction was cooled to ambient temperature and silica gel (20 g) was added followed by concentration under reduced pressure. The sample absorbed on silica was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-7% gradient of methanol in dichloromethane). The recovered solid was washed with 1% aqueous sodium carbonate to provide 1.95 g of 2-{2[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]ethenyl}-1H-isoindole-1,3(2H)-dione as a bright yellow solid. MS (APCI) m/z 441 (M+H)+.

Workup

  1. customA thick walled glass tube, equipped with a stir bar
  2. customThe reaction mixture was purged with nitrogen
  3. customthe tube was sealed
  4. temperatureThe reaction was cooled to ambient temperature
  5. additionsilica gel (20 g) was added
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe sample absorbed on silica
  8. customwas purified by chromatography
  9. washeluting with a 0-7% gradient of methanol in dichloromethane)
  10. washThe recovered solid was washed with 1% aqueous sodium carbonate

Sources & evidence

ORD record
ord-ff4a24d80ddc4e10830f292fdb3b4dad
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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