Diisopropylamine → 5-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

HRID 1916530

Reaction equation

[CH2:1]([C:5]1[CH:16]=[CH:15][C:8]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)[CH2:2][C:3]#[CH:4].Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=1.C(NC(C)C)(C)C>C1COCC1.O.[Cu]I>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:4]#[C:3][CH2:2][CH2:1][C:5]2[CH:16]=[CH:15][C:8]([CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=2)=[N:19][CH:20]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 200 mg (0.94 mmol) 1-(4-but-3-ynyl-benzyl)-pyrrolidine, 222 mg (0.94 mmol) 2,5-dibromopyridine, 13.2 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium, 3.6 mg (0.02 mmol) CuI and 0.27 mL diisopropylamine in 10 mL THF is heated for 4 h at 40° C. under an argon atmosphere. The reaction mixture is diluted with water, exhaustively extracted with EtOAc, the organic phase is washed with saturated, aqueous NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

Workup

extractionexhaustively extracted with EtOAc
washthe organic phase is washed with saturated, aqueous NaCl solution
dry with materialdried over Na2SO4
customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record: ord-e13c917bb04b4f3c8bd29402a92662eb
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Linked notes

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