Sodium Carbonate → 5-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

HRID 1916531Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[N:6][CH:7]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](OB(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:14][CH:13]=3)=[N:6][CH:7]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 100 mg (0.27 mmol) 5-bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine, 85 mg (0.54 mmol) 4-chloro-phenylboric acid, 15.7 mg (0.014 mmol) tetrakis-triphenylphosphane-palladium, 0.28 mL of a 2 M aqueous Na2CO3 solution in 10 mL 1,4-dioxane is heated for 8 h at 100° C. under an argon atmosphere. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified over neutral Alox (ICN Alumina N+5% H2O; cyc/EtOAc 7:3). The product fractions are evaporated down, the residue is triturated with PE and suction filtered.

Workup

distillationThe solvent is distilled off i.vac
extractionexhaustively extracted with EtOAc
dry with materialdried over Na2SO4
customis purified over neutral Alox (ICN Alumina N+5% H2O; cyc/EtOAc 7:3)
customThe product fractions are evaporated down
customthe residue is triturated with PE and suction
filtrationfiltered

Sources & evidence

ORD record: ord-a3a109de35a44f07b79f23a3caddfcf8
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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