Triethylamine → HCID 68683207, compound

HRID 1713793Notes

Reaction equation

HRID 1713793 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([OH:15])[CH2:12][C:13]#[CH:14].C(N(CC)CC)C>C(#N)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:14]#[C:13][CH2:12][CH2:11][OH:15])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 782402-Bromo-5-nitropyridine

Product 1

HCID 68683207HCID 68683207, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-5-nitro pyridine (2.03 g, 10 mmol), 3-butyn-1-ol (1.05 g, 15 mmol), copper(I) iodide (19 mg, 0.1 mmol), dichlorobis(triphenylphosphine)palladium (II) (140 mg, 0.02 mmol), triethylamine (5.06 g, 50 mmol) in acetonitrile (30 mL) was stirred for 4 h. The reaction mixture was evaporated to dryness and loaded onto a Biotage KPSil60A cartridge, and purified by flash chromatography using Et2O-DCM (1:9) as eluent to afford 4-(5-nitropyridin-2-yl)but-3-yn-1-ol as an oil (1.42 g, MS m/e MH+ 193). This oil (1 g, 5.21 mmol) was stirred in methanol (50 mL) and 10% palladium on carbon (0.2 g) was added and the reaction stirred under an atmosphere of hydrogen. The reaction was filtered through Celite® and concentrated in vacuo to afford the title compound as an oil (0.87 g). 1H NMR δ 7.99 (1H, s), 6.93 (2H, s), 3.86 (2H, t), 3.55 (2H, s), 2.73 (2H, t), 1.70-1.74 (2H, m), 1.60-1.62 (2H, m); MS m/e MH+ 167.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-be559b32c85248fba416707654f1a486
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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