2-Bromobenzonitrile → 2-[1-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-yl)-indan-5-yl]-benzonitrile

HRID 1742421Notes

Reaction equation

HRID 1742421 reaction equation
C([C:3]1[N:13]([CH:14]2[C:22]3[C:17](=[CH:18][C:19]([Sn](CCCC)(CCCC)CCCC)=[CH:20][CH:21]=3)[CH2:16][CH2:15]2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)C.Br[C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[C:39]#[N:40].O1CCO[CH2:47][CH2:46]1>>[CH2:46]([C:3]1[N:13]([CH:14]2[C:22]3[C:17](=[CH:18][C:19]([C:37]4[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=4[C:39]#[N:40])=[CH:20][CH:21]=3)[CH2:16][CH2:15]2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:47]

Participants

4

Reactant 3

HCID 162722-BromobenzonitrileHCID 312751,4-DioxaneHCID 190088972-ethyl-5,7-dimethyl-3-(5-tributylstannanyl-indan-1-yl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 190089182-[1-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-yl)-indan-5-yl]-benzonitrile

Conditions

Temperature
23 °C

Procedure

To a solution of 2-ethyl-5,7-dimethyl-3-(5-tributylstannanyl-indan-1-yl)-3H-imidazo[4,5-b]pyridine (264 mg, 0.48 mmol) in anhydrous dioxane (1.5 mL) was added 2-bromobenzonitrile (109 mg, 0.6 mmol) and PdCl2 (PPh3)2 (34 mg, 0.048 mmol). The reaction mixture was heated under reflux for 17 hours, cooled to 23° C. and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 30% ethyl acetate/hexanes to give 100 mg of the desired product. 1H NMR (250 MHz, CDCl3): d 7.75 (1H, m), 7.64 (1H, m), 7.55 (m, 2 H), 7.35 (t, 1 H), 7.00 (d, 1 H), 6.9 (s, 1 H), 6.6 (m, 1 H), 3.4 (m, 2 H), 2.95 (m, 1 H), 2.65 (s, 3 H), 2.58 (s, 3 H), 1.3 (t, 3 H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 17 hours
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-caef0d31a4a04b3fae64e855fe21e5c9
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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