Methyl Methacrylate → HCID 23321871, compound

HRID 280204Notes

Reaction equation

HRID 280204 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.[C:39]([O:44][CH3:45])(=[O:43])[C:40]([CH3:42])=[CH2:41]>C(N(CC)CC)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:39]([C:40](=[CH2:41])[CH2:42][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)([O:44][CH3:45])=[O:43]

Participants

7

Reactant 3

HCID 6658Methyl MethacrylateHCID 80271Tri-o-tolylphosphineHCID 13649438HCID 13649438, compound

Product 1

HCID 23321871HCID 23321871, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 0.34 g of 5-(p-bromophenyl)imidazo[1,5-a]pyridine, 2.7 mg of palladium acetate, 7.5 mg of tri-o-tolyphosphine and 0.22 g methyl methacrylate in 3 ml of triethylamine is refluxed for 7 days, diluted with 50 ml of methylene chloride and washed with water. The methylene chloride is evaporated and the residue is taken up in 50 ml ether, filtered and washed with 2×20 ml of ice-cold 0.5N hydrochloric acid. The aqueous phase is adjusted to pH=8 and is extracted with methylene chloride. The methylene chloride extract is dried over magnesium sulfate and evaporated. Preparative thin layer chromatography (silica gel, ether) yields 5-[p-(2-carbomethoxyprop-2-enyl)phenyl]imidazo[1,5-a]pyridine; Rf=0.37; NMR: (CDCl3) 5.62 (s, 1H), 6.32 (s, 1H); IR (CH2Cl2) 1720 cm-1.

Workup

  1. washwashed with water
  2. customThe methylene chloride is evaporated
  3. filtrationfiltered
  4. washwashed with 2×20 ml of ice-cold 0.5N hydrochloric acid
  5. extractionis extracted with methylene chloride
  6. extractionThe methylene chloride extract
  7. dry with materialis dried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-fd5c909424d9432bbbdda1d76f1623da
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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