Sodium Carbonate → HCID 12988663, compound

HRID 1916720Notes

Reaction equation

HRID 1916720 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)=[N:12][CH:13]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36](OB(O)O)=[CH:35][CH:34]=1>O1CCOCC1>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][CH2:16][N:17]3[C:25]4[C:20](=[CH:21][C:22]([CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:23][CH:24]=4)[CH:19]=[CH:18]3)=[N:12][CH:13]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 17810664p-Chlorophenylboric acidHCID 69069498HCID 69069498, compound

Product 1

HCID 12988663HCID 12988663, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Under an argon atmosphere 0.5 mL 2 M Na2CO3 solution and 10 mg (0.01 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 59 mg (0.15 mmol) 1-[3-(5-bromo-pyridin-2-yl)-prop-2-ynyl]-5-pyrrolidin-1-ylmethyl-1H-indole and 50 mg (0.32 mmol) 4-chlorophenyl-boric acid in 5 mL 1,4-dioxane and the reaction mixture is stirred for 2.5 h at 110° C. The mixture is evaporated down i. vac., the residue is combined with 3 mL water, extracted with 5 mL EtOAc, the organic phase is washed with saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by HPLC.

Workup

  1. customThe mixture is evaporated down i
  2. extractionextracted with 5 mL EtOAc
  3. washthe organic phase is washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customis purified by HPLC

Sources & evidence

ORD record
ord-a9e819b31cdb452b976a422519da79d4
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…