HCID 46739146, compound → HCID 66598526, compound

HRID 1189221Notes

Reaction equation

HRID 1189221 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[CH:5]=[CH:4][CH:3]=1.[CH2:11]([N:15]1[N:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]2=[N:16]1)[CH2:12][C:13]#[CH:14]>>[N:16]1[N:15]([CH2:11][CH2:12][C:13]#[C:14][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[CH:5]=[CH:4][CH:3]=2)[N:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=12

Participants

3

Reactant 2

HCID 46739146HCID 46739146, compoundHCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazole

Product 1

HCID 66598526HCID 66598526, compoundYield 24%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from (6-bromo-pyridin-2-yl)-ethyl-amine (100 mg, 0.50 mmol) and 2-but-3-ynyl-2H-benzo[d][1,2,3]triazole (0.13 g, 0.75 mmol, Example 109(D)). Reaction time: 3 hours. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3) to yield 35 mg (0.12 mmol, 24%) of 6-(4-(2H-benzo[d][1,2,3]triazol-2-yl)but-1-ynyl)-N-ethylpyridin-2-amine as a brown solid (M.P.=73-78° C.).

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3)

Sources & evidence

ORD record
ord-9e03d2940a884b0d955373d9a1f531bb
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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