Benzoic acid, 2-iodo-, methyl ester → 2-[1-(Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-yl)-indan-5-yl]-benzoic acid methyl ester

HRID 1742420Notes

Reaction equation

HRID 1742420 reaction equation
[CH2:1]([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)[CH3:2].I[C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40]>O1CCOCC1>[CH3:42][O:41][C:39](=[O:40])[C:38]1[CH:43]=[CH:44][CH:45]=[CH:46][C:37]=1[C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[CH:14]([N:13]1[C:6]3=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]3[N:4]=[C:3]1[CH2:1][CH3:2])[CH2:15][CH2:16]2

Participants

4

Reactant 2

HCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 190088972-ethyl-5,7-dimethyl-3-(5-tributylstannanyl-indan-1-yl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 678430742-[1-(Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-yl)-indan-5-yl]-benzoic acid methyl esterYield 28.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-ethyl-5,7-dimethyl-3-(5-tributylstannyl-indan-1-yl)-3H-imidazol[4,5-b]pyridine (224 mg, 0.41 mmol), methyl 2-iodobenzoate (131 mg, 0.5 mmol) and PdCl2 (PPh3)2 (28 mg, 0.04 mmol) was heated in anhydrous 1,4-dioxane for 20 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo and chromatographed on SiO2 -gel using a gradient of 30% EtOAc/hexanes to 50% EtOAc/hexanes to give 50 mg of a colorless oil. 1H NMR (250 MHz, CDCl3): d 7.80 (1 H, d), 7.55 (t, 1 H), 7.43 (t, 2 H), 7.30 (s, 1 H), 7.10 (d, 2 H), 6.90 (m, 2 H), 6.52 (m, 1H), 3.30 (m, 1 H), 3.15 (m, 1 H), 2.85 (q, 2 H), 2.65 (s, 3 H), 2.57 (s, 3 H), 0.90 (t, 3H.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customchromatographed on SiO2

Sources & evidence

ORD record
ord-3ff6f6ef341a4d99a5cb5257051540c5
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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