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

HRID 1916681Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-ca08ff5e8e644fb0a6682fece1d08456
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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