4-Vinylpyridine → HCID 68576099, compound

HRID 1948991Notes

Reaction equation

HRID 1948991 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH:6]=[CH:5]2.[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[CH2:23].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:23]=[CH:22]/[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH:3]=2)[N:8]=1

Participants

8

Reactant 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 68574436HCID 68574436, compound

Product 1

HCID 68576099HCID 68576099, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(6-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 2 mL dimethylformamide. 4-Vinylpyridine (80 mg, 0.762 mmol), triethylamine (77 mg, 0.760 mmol), tri-o-tolylphosphin (7 mg, 0.023 mmol) and palladium(II)acetate (3 mg, 0.013 mmol) were added. The reaction mixture was stirred in a sealed tube at 100° C. for 16 h. The reaction mixture was poured into 30 mL water and extracted three times with ethyl acetate (30 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient). The title compound was obtained as a light yellow solid (65 mg, 30%), MS: m/e=368.1 (M+H+).

Workup

  1. extractionextracted three times with ethyl acetate (30 mL each)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient)

Sources & evidence

ORD record
ord-fbd320cd49994b0f9ebe025478c6034e
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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