Triethylamine → 3-(2'-Cyanobiphenyl-3-yl)imidazo[1,2-alpha]pyridine-7-carbonitrile

HRID 985544Notes

Reaction equation

HRID 985544 reaction equation
O[N:2]=[CH:3][C:4]1[CH:9]=[CH:8][N:7]2[C:10]([C:13]3[CH:14]=[C:15]([C:19]4[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:16]=[CH:17][CH:18]=3)=[CH:11][N:12]=[C:6]2[CH:5]=1.C(N(CC)CC)C.C(N1C=CN=C1)(N1C=CN=C1)=O>ClCCl>[NH3:2].[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:10]2[N:7]3[CH:8]=[CH:9][C:4]([C:3]#[N:2])=[CH:5][C:6]3=[N:12][CH:11]=2)[CH:14]=1)#[N:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 1364734673'-(7-Hydroxyiminomethylimidazo [1,2-alpha]pyridin-3-yl)biphenyl-2-carbonitrile

Product 2

HCID 222AmmoniaHCID 1317248083-(2'-Cyanobiphenyl-3-yl)imidazo[1,2-alpha]pyridine-7-carbonitrileYield 171.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3′-(7-Hydroxyiminomethylimidazo[1,2-α]pyridin-3-yl)biphenyl-2-carbonitrile (105 mg, 0.31 mmol), triethylamine (157 mg, 1.55 mmol) and 1,1′-carbonyldiimidazole (252 mg, 1.55 mmol) were dissolved in dichloromethane (5 ml) and stirred at room temperature for 15 min then heated under reflux for 2.5 h. The mixture was cooled to ambient temperature, diluted with dichloromethane (40 ml) and washed with water (40 ml) and brine (40 ml). The organics were dried over anhydrous sodium sulfate and evaporated to dryness. Purification of this material by preparative thin-layer chromatography eluting with dichloromethane/methanol/conc. ammonia (98:2:0.2) gave the title compound (85 mg, 86%) as a white solid. 1H NMR (400 MHz, CDCl3) δH 7.03 (1H, dd, J 1 and 7), 7.52 (1H, dt, J 8 and 1), 7.58 (1H, d, J 7), 7.62-7.66 (2H, m), 7.69-7.74 (2H, m), 7.79-7.84 (2H, m), 7.97 (1H, s), 8.12 (1H, s), 8.69 (1H, d, J 7); m/z (ES+) 321 (M++H).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 2.5 h
  3. temperatureThe mixture was cooled to ambient temperature
  4. washwashed with water (40 ml) and brine (40 ml)
  5. dry with materialThe organics were dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customPurification of this material by preparative thin-layer chromatography
  8. washeluting with dichloromethane/methanol/conc

Sources & evidence

ORD record
ord-3e197afdcc5a4c97ae642dd95a7298bd
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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