Styrene → HCID 66808472, compound

HRID 607323Notes

Reaction equation

HRID 607323 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:18]=[CH:17][C:16]([CH3:19])=[N:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][C:16]1[CH:17]=[CH:18][C:10]2[C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH:20]=[CH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:3]=3)=[N:14][CH:13]=[N:12][C:11]=2[N:15]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 66808549HCID 66808549, compound

Product 1

HCID 66808472HCID 66808472, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the product from Example 240A (0.063 g, 0.20 mmol), styrene (0.0412 g, 0.40 mmol, 2.0 eq), palladium(II) acetate (0.9 mg, 0.004 mmol, 0.02 eq), tri-o-tolylphosphine (2.4 mg, 0.008 mmol, 0.04 eq), and triethylamine (0.0607 g, 0.60 mmol, 3.0 eq) in dimethylformamide (2 mL) was heated in a 120° C. oil bath for 4 hours. The mixture was then cooled to room temperature and the solvent evaporated under a stream of nitrogen gas. The residue was partitioned between ethyl acetate and water and the aqueous layer further extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was recrystallized from methanol and dried to provide the title compound as yellow crystals (11.8 mg, 17%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.01 (s, 1H), 8.89 (d, J=8.46 Hz, 1H), 8.72 (s, 1H), 8.03 (s, 1H), 7.72-7.85 (m, J=6.07, 2.76 Hz, 1H), 7.64 (d, J=6.99 Hz, 2H), 7.57 (d, J=8.82 Hz, 1H), 7.35-7.49 (m, 4H), 7.24-7.35 (m, 3H), 2.63-2.74 (m, 3H); MS (ESI+) m/z 339.1 (M+H)+, (ESI−) m/z 337.1 (M−H)−.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customthe solvent evaporated under a stream of nitrogen gas
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionthe aqueous layer further extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized from methanol
  9. customdried

Sources & evidence

ORD record
ord-1e25383b28cc4f228fdd23b893532532
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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