2-Iodo-5-methoxypyridine → 7-Chloro-2-(5-methoxypyridin-2-yl)thieno[3,2-b]pyridine

HRID 985243Notes

Reaction equation

HRID 985243 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn](C)(C)C)[S:10][C:3]=12.I[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][N:17]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][N:17]=3)[S:10][C:3]=12

Participants

3

Reactant 2

HCID 70107332-Iodo-5-methoxypyridineHCID 221434977-Chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 221436607-Chloro-2-(5-methoxypyridin-2-yl)thieno[3,2-b]pyridineYield 34%

Procedure

This material was prepared by coupling 7-chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine 39a (0.214 g, 0.64 mmole) with 2-iodo-5-methoxypyridine (0.152 g, 0.64 mmole) using tereakis (triphenylphosphine)palladium(0) (30 mg) as catalyst in a manner as previously described for example 39b to give a yellow solid (0.060 g, 34%). 1H NMR (300 MHz, CDCl3) δ8.55 (1H, d, J=5.1 Hz), 8.43 (1H, s), 8.28 (1H, dd, J=1.3, 4.6 Hz), 7.34 (1H, m), 7.28 (1H, m), 7.24 (1H, d, J=5.8 Hz), 4.04 (3H, s).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-5824aaa0dea84363871696712013feb9
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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