6-Bromopyridine-2-carbaldehyde → HCID 22143597, compound

HRID 1825126Notes

Reaction equation

HRID 1825126 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[N:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][CH:17]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:16]3[N:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][CH:17]=3)[S:10][C:3]=12

Participants

3

Reactant 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 221434977-Chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 22143597HCID 22143597, compoundYield 27%

Procedure

This material was prepared by coupling 7-chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine 39a (0.707 g, 2.17 mmole) with 6-bromopyridine-2-carbaldehyde (0.396 g, 2.17 mmole) using tereakis(triphenylphosphine)palladium(0) (100 mg) as catalyst in a manner as previously described for example 39b to give a white solid (0.161 g, 27%). 1H NMR (300 MHz, CDCl3) δ 10.15 (1H, s), 8.61 (1H, d, J=5.1 Hz), 7.93–8.09 (4H, m) 7.31 (1H, d, J=5.1 Hz); ESIMS (MH+): 275.00.

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-879c2e3565b047939eb9c11624a420ff
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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