2-(6-Bromohex-1-ynyl)pyridine → HCID 66598079, compound

HRID 422367Notes

Reaction equation

HRID 422367 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[NH:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1>C1CCCCC1.CCOC(C)=O>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]#[C:6][CH2:5][CH2:4][CH2:3][CH2:2][N:15]1[N:16]=[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]2=[N:14]1

Participants

4

Reactant 2

HCID 203312122-(6-Bromohex-1-ynyl)pyridineHCID 178418385HCID 178418385, compound

Product 1

HCID 66598079HCID 66598079, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

The title compounds were prepared, in accordance with the general method of Example 109(D), from 2-(6-bromo-hex-1-ynyl)-pyridine (250 mg, 1.05 mmol) and benzotriazole (125 mg, 1.05 mmol). The crude product was purified by flash chromatography (cyclohexane/AcOEt 3:2) to yield 2-(6-(pyridin-2-yl)hex-5-ynyl)-2H-benzo[d][1,2,3]triazole (38 mg, 0.14 mmol, 13%) as a brown oil and (cyclohexane/AcOEt 1:1) to yield 1-(6-(pyridin-2-yl)hex-5-ynyl)-1H-benzo[d][1,2,3]triazole (48 mg, 0.17 mmol, 16%) as a brown oil.

Workup

  1. customThe crude product was purified by flash chromatography (cyclohexane/AcOEt 3:2)

Sources & evidence

ORD record
ord-f849659441cb48ecb77aa1f8cd63d459
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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