Sodium Carbonate → HCID 21830685, compound

HRID 1600930Notes

Reaction equation

HRID 1600930 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:32]=[CH:31][C:11]([O:12][CH2:13][CH:14]([O:23][Si](C(C)(C)C)(C)C)[CH2:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:10][CH:9]=1.[Cl:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[C:38]([Cl:40])[CH:39]=1.F>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.C1(C)C=CC=CC=1>[Cl:33][C:34]1[CH:35]=[C:36]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH:14]([OH:23])[CH2:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:31][CH:32]=2)[CH:37]=[C:38]([Cl:40])[CH:39]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 14917Hydrofluoric AcidHCID 27343313,5-Dichlorophenylboronic acidHCID 21717163HCID 21717163, compound

Product 1

HCID 21830685HCID 21830685, compoundYield 78.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

Prepared according to the method described in Example 33a) from toluene (3 ml), aqueous sodium carbonate (2 M, 1.4 ml), (±)-3-(4-(4-bromophenoxy)-3-(tert-butyldimethylsilyloxy)butyl)pyridine (0.67 g), ethanol (0.8 ml), 3,5-dichlorobenzeneboronic acid (0.30 g) and tetrakis(triphenylphosphine)palladium(0) (73 mg) with heating at 120° C. for 6 hours. The residue obtained after work up was deprotected as in Example 34e) using hydrofluoric acid (40%, 4 ml) in acetonitrile (30 ml). The residue obtained after work up was purified by column chromatography over silica eluting with dichloromethane then ether then ethyl acetate to give an oil (0.47 g). This was recrystallised from ether to give the title compound as a white solid (0.21 g).

Workup

  1. customPrepared
  2. customThe residue obtained after work
  3. customThe residue obtained after work
  4. customup was purified by column chromatography over silica eluting with dichloromethane

Sources & evidence

ORD record
ord-b1edf844b37a4003819bdbce61b969ef
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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