Imidazole → 3-((1H-imidazol-1-yl)methyl)-6-phenylpyridazine

HRID 1054112Notes

Reaction equation

HRID 1054112 reaction equation
Br[CH2:2][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N:15]1([CH2:2][C:3]2[N:4]=[N:5][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:7][CH:8]=2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 667174453-(Bromomethyl)-6-phenylpyridazine

Product 1

HCID 573300783-((1H-imidazol-1-yl)methyl)-6-phenylpyridazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized using compound 65a (40 mg, 0.16 mmol), imidazole (44 mg, 0.64 mmol) and K2CO3 (111 mg, 0.80 mmol) in acetonitrile according to Method B. Crude product was purified by flash chromatography on silica-gel using ethyl acetate as eluent. After flash chromatography the solid was washed with ethyl acetate. Light orange solid. Yield: 22 mg, 58%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=5.58 (s, 2H), 7.08 (s, 1H), 7.17-7.26 (m, 2H), 7.55-7.61 (m, 3H), 7.72 (s, 1H), 7.88 (d, J=8.8 Hz, 1H), 8.09-8.14 (m, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=50.9, 119.6, 125.1, 125.5, 127.4, 129.4, 130.7, 130.8, 135.8, 137.8, 157.2, 159.3; (ESI): m/z=236.91 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. washAfter flash chromatography the solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-7461a82abea0479497936376520f1983
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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