2-Chloro-3-fluoropyridine → 2-(4-(3-fluoropyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole

HRID 334659Notes

Reaction equation

HRID 334659 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=[N:14]1)[CH2:10][C:11]#[CH:12]>>[F:8][C:7]1[C:2]([C:12]#[C:11][CH2:10][CH2:9][N:13]2[N:14]=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=[N:17]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 27827912-Chloro-3-fluoropyridineHCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665980942-(4-(3-fluoropyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 27.6%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-chloro-3-fluoropyridine (42 mg, 0.32 mmol) and 2-(but-3-ynyl)-2H-benzo[d][1,2,3]triazole (50 mg, 0.29 mmol, Example 109(D)). Reaction time: 13 hours. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 21 mg (80 μmol, 27%) of 2-(4-(3-fluoropyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a yellow solid.

Workup

  1. customReaction time
  2. custom13 hours
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-88299ac5e5174ee4bd420abfc82f880a
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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