3-Bromo-7-chloroimidazo[1,2-a]pyridine → 7-Chloro-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

HRID 985524Notes

Reaction equation

HRID 985524 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]2=[N:4][CH:3]=1.C(O)(=O)C(O)=O.C([Sn](CCCC)(CCCC)[C:23]1[CH:24]=[C:25]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1)CCC>CCO>[Cl:11][C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:27]3[CH:28]=[CH:23][CH:24]=[C:25]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[CH:26]=3)=[CH:3][N:4]=[C:5]2[CH:10]=1

Participants

4

Reactant 2

HCID 467391183-Bromo-7-chloroimidazo[1,2-a]pyridineHCID 1317248063-[3-(tri-n-butylstannanyl)phenyl]pyridine. Oxalate salt

Product 1

HCID 99011257-Chloro-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in a similar manner to that described in Example 11 from 3-bromo-7-chloroimidazo[1,2-α]pyridine and 3-[3-(tri-n-butylstannanyl)phenyl]pyridine. Oxalate salt, white crystalline solid, m.p. 178-180° C. (EtOH). 1H NMR (360 MHz, d6-DMSO) δH 7.05 (1H, dd, J 7 and 2), 7.50-7.56 (1H, m), 7.67-7.89 (4H, m), 7.96 (1H, s), 8.01 (1H, s), 8.21 (1H, d, J 7), 8.61 (1H, d, J 4), 8.70 (1H, d, J 7), 9.02 (1H, d, J 2); m/z (ES+) 306 (M++H).

Sources & evidence

ORD record
ord-9974dd910f9144f987c5573344ad79bd
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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