Water → 4-(5-Bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol

HRID 1916723Notes

Reaction equation

HRID 1916723 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].Br[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.C(NC(C)C)(C)C.O>C1COCC1.[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>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]#[C:4][C:2]([CH3:3])([OH:6])[CH3:1])=[N:9][CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 82582-Methyl-3-butyn-2-olHCID 693532,5-Dibromopyridine

Product 1

HCID 225024714-(5-Bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 38 mg (0.2 mmol) CuI and 143 mg (0.2 mmol) Pd(PPh3)2Cl2 are added to a solution of 0.99 mL (10.0 mmol) 2-methyl-but-3-yn-2-ol and 2.44 g (10.0 mmol) 2,5-dibromo-pyridine in 50 mL THF and 2.8 mL (20 mmol) diisopropylamine and the reaction mixture is stirred for 15 min at RT. The reaction mixture is combined with water, exhaustively extracted with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 2:1).

Workup

  1. extractionexhaustively extracted with EtOAc
  2. dry with materialthe organic phase is dried over Na2SO4
  3. customis purified by chromatography (silica gel, cyc/EtOAc 2:1)

Sources & evidence

ORD record
ord-f84fc523022a4a0194b2398148db7467
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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