1H-Indazole → HCID 66598141, compound

HRID 334644Notes

Reaction equation

HRID 334644 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:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH: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[CH:16]=[C:17]2[C:22]([CH:21]=[CH:20][CH:19]=[CH:18]2)=[N:14]1

Participants

4

Reactant 2

HCID 92211H-IndazoleHCID 203312122-(6-Bromohex-1-ynyl)pyridine

Product 1

HCID 66598141HCID 66598141, compoundYield 9%

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, Example 124(B)) and indazole (124 mg, 1.05 mmol). The crude product was purified by flash chromatography (cyclohexane/AcOEt 75:25) to yield 2-(6-(pyridin-2-yl)hex-5-ynyl)-2H-indazole (26 mg, 94 μmol, 9%) as a brown oil and (cyclohexane/AcOEt 1:1) to yield 1-(6-(pyridin-2-yl)hex-5-ynyl)-1H-indazole (15 mg, 54 μmol, 5%) as a brown oil.

Workup

  1. customThe crude product was purified by flash chromatography (cyclohexane/AcOEt 75:25)

Sources & evidence

ORD record
ord-5a5da9bd25b24107b3a61520ef063b2f
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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