HCID 21106086, compound → 5-Naphthalen-1-yl-imidazo[1,5-a]pyridine

HRID 2235017Notes

Reaction equation

HRID 2235017 reaction equation
C(S[C:4]1[N:8]2[C:9]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[CH:10][CH:11]=[CH:12][C:7]2=[CH:6][N:5]=1)C>[Ni].C(O)C>[C:13]1([C:9]2[N:8]3[CH:4]=[N:5][CH:6]=[C:7]3[CH:12]=[CH:11][CH:10]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 21106086HCID 21106086, compound

Product 1

HCID 98377265-Naphthalen-1-yl-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

Raney Nickel suspension (1 mL, Fluka Cat. No. 83440) is added to a solution of the title D compound, 3-ethylsulfanyl-5-naphthalen-1-yl-imidazo[1,5-a]pyridine (268 mg, 0.88 mmol) in ethanol (15 mL) and heated at reflux overnight. Additional Raney Nickel (1 mL) is added, and the reaction mixture is heated at reflux for three days further, until MS showed complete disappearance of the starting material. The catalyst is filtered off and washed with ethanol. The combined filtrates are concentrated under reduced pressure. The residue is purified by flash column chromatography on silica using ethyl ether as the eluant to yield 5-naphthalen-1-yl-imidazo[1,5-a]pyridine as an amber film. The hydrochloride salt is prepared in acetone by addition of an ethereal solution of HCl (1.2 eq.). The resulting precipitate is re-crystallized from acetonitrile to yield 5-naphthalen-1-yl-imidazo[1,5-a]pyridine hydrochloride (m.p.222-223° C.): 1H-NMR, (MeOH-d4) δ 8.71 (s, 1H), 8.21 (d, J=8.1, 1H), 8.16 (s, 1H), 8.13 (d, J=16.3, 1H), 8.04 (d, J=17, 1H), 7.98-7.70 (m, 2H), 7.61 (dt, J=5.6,1.2, 1H); 7.53-7.40, m, (3H); 7.28 (d, J=7.7, 1H); 13C-NMR (MeOH-d4) δ 135.8, 135.53, 132.84, 132.68, 131.96, 130.34, 130.13, 129.81, 129.11, 128.15, 127.04, 126.18, 125.60, 124.79, 120.93, 119.43, 116.50, 112.96; MS (M+1)+ 245.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for three days further
  5. filtrationThe catalyst is filtered off
  6. washwashed with ethanol
  7. concentrationThe combined filtrates are concentrated under reduced pressure
  8. customThe residue is purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-ac34c9c1bc5e4e47b648f1680b3837fe
Source dataset
uspto-grants-2010_05
Patent number
US07713991B2

Reaction notes

Loading…