2-Bromo-6-methylpyridin-3-amine → (2-(5-Chloro-pyridin-3-ylethynyl)-6-methyl-pyridin-3-yl)amine

HRID 1271567Notes

Reaction equation

HRID 1271567 reaction equation
Br[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:17]#[CH:18])[CH:16]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:10][C:11]1[CH:16]=[C:15]([C:17]#[C:18][C:2]2[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=2)[CH:14]=[N:13][CH:12]=1

Participants

5

Reactant 2

HCID 144180512-Bromo-6-methylpyridin-3-amineHCID 235008873-Chloro-5-ethynylpyridine

Product 1

HCID 10332043(2-(5-Chloro-pyridin-3-ylethynyl)-6-methyl-pyridin-3-yl)amineYield 72.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Following the same procedure as described in Example 1, (2-bromo-6-methyl-pyridin-3-yl)amine (150 mg, 0.80 mmol) reacted with (PPh3)2PdCl2 (28 mg, 40 μmol), Cul (8 mg, 40 μmol) and 3-chloro-5-ethynyl-pyridine (165 mg, 1.20 mmol) in triethylamine (5 ml). The crude residue was purified by flash chromatography (hexane/ethyl acetate 7:3) to yield 141 mg (0.58 mmol, 72%) of (2-(5-chloro-pyridin-3-ylethynyl)-6-methyl-pyridin-3-yl)amine as a yellow solid.

Workup

  1. customThe crude residue was purified by flash chromatography (hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-2739a8c0ed9a4234b83e4fc02b4d146b
Source dataset
uspto-grants-2007_04
Patent number
US07205411B2

Reaction notes

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