2-Bromopyridine → 2-(4-(Pyridin-2-yl)but-3-ynyl)benzo[d]oxazole

HRID 1189060Notes

Reaction equation

HRID 1189060 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)[CH2:9][C:10]#[CH:11].C1C=CN/C(=C\N=O)/C=1>C(Cl)Cl>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 860869072-(But-3-ynyl)benzo[d]oxazoleHCID 178526334HCID 178526334, compound

Product 1

HCID 116373832-(4-(Pyridin-2-yl)but-3-ynyl)benzo[d]oxazoleYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (746 mg, 4.67 mmol) and 2-(but-3-ynyl)benzo[d]oxazole (800 mg, 4.67 mmol). Reaction time: 3 hours. The crude residue was dissolved in DCM, syn-2-pyridinecarboxaldoxime (684 mg, 5.60 mmol) was added and the reaction mixture was stirred overnight. The solvent was evaporated and the resulting crude product was purified by flash chromatography (DCM/MeOH 99:1) to yield 923 mg (3.72 mmol, 79%) of 2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole as a yellow solid.

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe solvent was evaporated
  4. customthe resulting crude product was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-5718095a0119439b95bb2185f960d321
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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