HCID 21106086, compound → HCID 9837726, compound

HRID 1354571Notes

Reaction equation

HRID 1354571 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 9837726HCID 9837726, compound

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-27b3276412b045e3b199a8653ac6153c
Source dataset
uspto-grants-2007_05
Patent number
US07223866B2

Reaction notes

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