Sodium Carbonate → HCID 59835766, compound

HRID 1916519Notes

Reaction equation

HRID 1916519 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:23]=[CH:22][C:13]([O:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH2:18]([N:17]([CH2:20][CH3:21])[CH2:16][CH2:15][O:14][C:13]1[CH:22]=[CH:23][C:10]([C:9]#[C:8][C:5]2[CH:4]=[CH:3][C:2]([C:29]3[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=3)=[CH:7][N:6]=2)=[CH:11][CH:12]=1)[CH3:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 147699944-Methoxyphenyl boric acidHCID 67364555HCID 67364555, compound

Product 1

HCID 59835766HCID 59835766, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 200 mg (0.54 mmol) {2-[4-(5-bromo-pyridin-2-ylethynyl)-phenoxy]-ethyl}-diethyl-amine, 163 mg (1.07 mmol) 4-methoxy-phenylboric acid, 31 mg (0.03 mmol) tetrakis-triphenylphosphane-palladium and 0.27 mL of a 2 M aqueous Na2CO3 solution in 5 mL 1,4-dioxane is heated for 20 h at 110° C. under a nitrogen 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 on silica gel (EtOAc/MeOH/NH3 95:5:0.5). The product fractions are evaporated down, the residue is triturated with diethyl ether, suction filtered and washed with diisopropylether.

Workup

  1. distillationThe solvent is distilled off i.vac
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)
  5. customThe product fractions are evaporated down
  6. customthe residue is triturated with diethyl ether, suction
  7. filtrationfiltered
  8. washwashed with diisopropylether

Sources & evidence

ORD record
ord-2af38873b4294c50891ff4fccd415818
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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