Triethylamine → [5-(4-Chloro-2-methyl-pyridin-3-ylethynyl)-pyridin-2-yl]-methyl-amine

HRID 1529210Notes

Reaction equation

HRID 1529210 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1I.[C:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH3:19])=[N:16][CH:17]=1)#[CH:11].C(N(CC)CC)C>CN(C=O)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:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[C:11]#[C:10][C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH3:19])=[N:16][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 226631285-ethynyl-N-methylpyridin-2-amineHCID 589309514-Chloro-3-iodo-2-methylpyridine

Product 1

HCID 70214860[5-(4-Chloro-2-methyl-pyridin-3-ylethynyl)-pyridin-2-yl]-methyl-amine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP1 starting from 20 mg (0.08 mmol) 4-chloro-3-iodo-2-methyl-pyridine and 11 mg (0.09 mmol) (5-Ethynyl-pyridin-2-yl)-methyl-amine using 1.5 mg (0.01 mmol) CuI, 5.5 mg (0.01 mmol) PdCl2(PPh3)2 and 0.11 mL (0.8 mmol) triethylamine in 1 mL dry DMF. After completion of the reaction the product is purified by RP-HPLC using a ACN/H2O gradient (95:5 to 70:30). Yield: 20 mg (98%).

Workup

  1. customAfter completion of the reaction the product
  2. customis purified by RP-HPLC

Sources & evidence

ORD record
ord-3d4ce6d3a5204220829f8345d2372d71
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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