2-Bromo-6-methylpyridin-3-amine → 2-(4-(2H-benzo[d][1,2,3]triazol-2-yl)but-1-ynyl)-6-methylpyridin-3-amine

HRID 334682

Reaction equation

HRID 334682 reaction equation
Br[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[CH2:10]([N:14]1[N:18]=[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]2=[N:15]1)[CH2:11][C:12]#[CH:13]>>[N:15]1[N:14]([CH2:10][CH2:11][C:12]#[C:13][C:2]2[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=2)[N:18]=[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=12

Participants

3

Reactant 2

HCID 144180512-Bromo-6-methylpyridin-3-amineHCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665978602-(4-(2H-benzo[d][1,2,3]triazol-2-yl)but-1-ynyl)-6-methylpyridin-3-amineYield 45%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-6-methyl-pyridin-3-ylamine (80 mg, 0.43 mmol) and 2-but-3-ynyl-2H-benzo[d][1,2,3]triazole (73 mg, 0.43 mmol, Example 109(D)). Reaction time: 3 hours. The crude residue was purified by flash chromatography (DCM/AcOEt 1:1) to yield 53 mg (0.19 mmol, 45%) of 2-(4-(2H-benzo[d][1,2,3]triazol-2-yl)but-1-ynyl)-6-methylpyridin-3-amine as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-d431e733744b4904a65964c96f97b211
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Linked notes

Loading…