Imidazole → 3-Cyano-1-(4-imidazol-1-yl-benzoyl)-pyrrolo[1,2-a]quinoline

HRID 720415Notes

Reaction equation

HRID 720415 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].C(=O)([O-])[O-].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 19660Carbonate IonHCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

Product 1

HCID 218921063-Cyano-1-(4-imidazol-1-yl-benzoyl)-pyrrolo[1,2-a]quinolineYield 76.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-cyano-(4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline (8 mg, 0.025 mmol), pottasium carbonate (10 mg, 0.072 mmol) and imidazole (5 mg, 0.073 mmol) were heated in 500 μL of DMF overnight. The reaction mixture was cooled to room temperature, diluted with 10 mL of ethyl acetate, washed with water (3×10 mL), saturated NaCl and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated. The crude was purified by chromatography (3% methanol/chloroform) to yield the title compound (6.9 mg, 75%). 1H NMR (CDCl3): 8.21 (dt, J=7.80, 1.20 Hz, 2H), 8.08 (d, J=8.72 Hz, 1H), 8.02 (s, 1H), 7.87 (dd, J=7.81, 1.82 Hz, 1H), 7.73 (m, 2H), 7.60 (m, 4H), 7.46 (s, 1H), 7.42 (t, J=1.24 Hz, 1H), 7.30 (s, 1H).

Workup

  1. washwashed with water (3×10 mL), saturated NaCl
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-107b03b101804228b89eaed877375598
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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