3-[3-(Tri-n-butylstannanyl)phenyl]pyridine → 7-Methoxy-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

HRID 985531Notes

Reaction equation

HRID 985531 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]2=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[CH:19]=[C:20]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:22][CH:23]=1)CCC>>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:22]3[CH:23]=[CH:18][CH:19]=[C:20]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:21]=3)=[CH:3][N:4]=[C:5]2[CH:10]=1

Participants

3

Reactant 2

HCID 225070873-[3-(Tri-n-butylstannanyl)phenyl]pyridineHCID 547755773-Bromo-7-methoxyimidazo[1,2-a]pyridine

Product 1

HCID 98794217-Methoxy-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

Procedure

The title compound was prepared in a similar manner to that described in Example 11 from 3-bromo-7-methoxyimidazo[1,2-α]pyridine and 3-[3-(tri-n-butylstannanyl)phenyl]pyridine to furnish a white crystalline solid, m.p. 153-154° C. 1H NMR (360 MHz, CDCl3) δH 3.89 (3H, s), 6.57 (1H, dd, J 2 and 8), 6.94 (1H, d, J 2), 7.37-7.43 (1H, m), 7.55-763 (4H, m), 7.72 (1H, s), 7.89-7.94 (1H, m), 8.19 (1H, d, J 7), 8.62-8.65 (1H, m), 8.90 (1H, s); m/z (ES+) 302 (M++H).

Workup

  1. customto furnish a white crystalline solid, m.p. 153-154° C

Sources & evidence

ORD record
ord-40a3f941fec749e2a489dfd088d1e9bb
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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