Sodium Carbonate → HCID 59835841, compound

HRID 271711Notes

Reaction equation

HRID 271711 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CO>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:21]2[CH:22]=[CH:23][C:18]([C:17]#[C:16][C:4]3[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)=[C:2]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH:3]=3)=[N:19][CH:20]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 10322966HCID 10322966, compound

Product 1

HCID 59835841HCID 59835841, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

30 mg (0.24 mmol) pyridine-3-boric acid are added to a solution of 115 mg (0.24 mmol) 2-[3-bromo-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-5-(4-chloro-phenyl)-pyridine (see Example 3.7), 0.5 mL (1.00 mmol) of a 2 M Na2CO3 solution and 15 mg (0.24 mmol) tetrakis-triphenylphosphane-palladium in 1 mL 1,4-dioxane and 0.3 mL methanol. The reaction mixture is refluxed for 6 h. After filtration the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH/NH3 1:1:0.1).

Workup

  1. temperatureThe reaction mixture is refluxed for 6 h
  2. filtrationAfter filtration the solvent
  3. customThe purification

Sources & evidence

ORD record
ord-d7073e6627a547c184c3b825a5e2d243
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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