2-Bromothiazole → 7-Chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridine

HRID 1825113Notes

Reaction equation

HRID 1825113 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.Br[C:16]1[S:17][CH:18]=[CH:19][N:20]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:16]3[S:17][CH:18]=[CH:19][N:20]=3)[S:10][C:3]=12

Participants

3

Reactant 2

HCID 764302-BromothiazoleHCID 221434977-Chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 221436637-Chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridineYield 46.2%

Procedure

This material was prepared by coupling of 7-chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine 39a (0.140 g, 0.42 mmole) and 2-bromo-1,3-thiazole (0.038 ml, 0.42 mmole) with tereakis(triphenylphosphine)palladium(0.019 g) in a manner as previously described in example 39b to give a yellow solid (0.049 g, 46%). 1H NMR (300 MHz, CDCl3) δ 8.59 (1H, d, J=5.1 Hz), 7.93 (1H, s), 7.89 (1H, d, J=3.4 Hz), 7.45 (1H, d, J=3.4 Hz), 7.30 (1H, d, J=5.1 Hz).

Sources & evidence

ORD record
ord-f0db0ce3e4d34743b1110d61385fbd3c
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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