Triethylamine → HCID 59681761, compound

HRID 1394221Notes

Reaction equation

HRID 1394221 reaction equation
Br[C:2]1[C:3]2[N:10]([CH2:11][CH3:12])[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[CH2:26])=[CH:23][CH:22]=1.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([N:10]1[C:3]2[C:2](/[CH:26]=[CH:25]/[C:24]3[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)=[CH:7][N:6]=[CH:5][C:4]=2[N:8]=[C:9]1[C:13]1[C:14]([NH2:18])=[N:15][O:16][N:17]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 125074-MethoxystyreneHCID 443971924-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine

Product 1

HCID 59681761HCID 59681761, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The product of example 100 (309 mg, 1 mmol), 4-methoxystyrene (167 uL, 1.25 mmol), palladium(II) acetate (12 mg, 0.05 mmol), o-tolyltriphenylphosphine (30 mg, 0.10 mmol) and triethylamine (349 uL, 2.5 mmol) were heated at 130° C. for 4 hours. The solution was partitioned between ethyl acetate and water, extracting with ethylacetate (×3). Combined extracts were washed with water (×3), brine, dried over anhydrous magnesium sulfate and concentrated to a crude solid, 450 mg, then purified by column chromatography eluting with 1:9:90.880 ammonia:ethanol:dichloromethane affording the title product, 176 mg (49%); MS (ES+) m/e 363 [M+H]+.

Workup

  1. customThe solution was partitioned between ethyl acetate and water
  2. extractionextracting with ethylacetate (×3)
  3. washCombined extracts were washed with water (×3), brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to a crude solid, 450 mg
  6. custompurified by column chromatography
  7. washeluting with 1:9:90.880 ammonia

Sources & evidence

ORD record
ord-5b2fa2a205cf485c993883d0023fce0e
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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