4-Bromopyridine → HCID 18354346, compound

HRID 429305Notes

Reaction equation

HRID 429305 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][C:16]([Sn](C)(C)C)=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.Br[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>CN(C=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][C:16]([C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 142684-BromopyridineHCID 18354371HCID 18354371, compound

Product 1

HCID 18354346HCID 18354346, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 80271Tri-o-tolylphosphineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Methylthio-4-[5-trimethylstannyl-benzimidazol-1-yl]pyrimidine (150 mg), 4-bromopyridine (180 mg), tri-o-tolylphosphine (5 mg) and tris(dibenzylidineacetone)dipalladium(0) (7.5 mg) were dissolved in DMF (3 mL) and heated to 100° C. for 1 hour. Upon cooling to rn and evaporation of solvent, the reaction residue was directly purified by column chromatography (SiO2,5% MeOH in CH2Cl2) to yield 100 mg of the title compound. Mass spectrum (ESI) 320.2 (M+1).

Workup

  1. temperatureUpon cooling to rn and
  2. customevaporation of solvent
  3. customthe reaction residue was directly purified by column chromatography (SiO2,5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e6deb0e95a53463ca118ec426d69da9e
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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