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Sodium Carbonate → 2-{4-[2-(4-Methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-5-phenyl-pyridine

HRID 271712
Notes
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Reaction equation

HRID 271712 reaction equation
[C:1]1(OB(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH2:30]3)=[CH:22][CH:21]=2)=[N:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CO.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:35][CH:32]1[CH2:33][CH2:34][N:29]([CH2:28][CH2:27][O:26][C:23]2[CH:24]=[CH:25][C:20]([C:19]#[C:18][C:15]3[CH:14]=[CH:13][C:12]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:17][N:16]=3)=[CH:21][CH:22]=2)[CH2:30][CH2:31]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 690601725-Bromo-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridine

Product 1

HCID 598357442-{4-[2-(4-Methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-5-phenyl-pyridine

Reagents, catalysts & solvents 4

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 887MethanolSolvent
HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon atmosphere 30 mg (0.25 mmol) phenylboric acid are added to a solution of 100 mg (0.25 mmol) 5-bromo-2-{4-[2-(4-methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine, 0.25 mL (0.50 mmol) of a 2 M Na2CO3 solution and 4 mg (0.01 mmol) Pd(dppf)Cl2 in 5 mL 1,4-dioxane and 2 mL MeOH. The reaction mixture is stirred for 3 days at 90° C. The reaction mixture is diluted with EtOAc and the organic phase is washed with 40 mL water and finally with saturated NaCl solution. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out using HPLC-MS and by column chromatography on silica gel (gradient: DCM/MeOH/NH3 95:5:0.5 to DCM/MeOH/NH3 9:1:0.1).

Workup

  1. washthe organic phase is washed with 40 mL water and finally with saturated NaCl solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe purification

Sources & evidence

ORD record
ord-4f7947abfcbd4537b04dd71808da0a2c
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07452911B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes