Sodium Carbonate → HCID 86621476, compound

HRID 1435070Notes

Reaction equation

HRID 1435070 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([C:18]#[N:19])[CH:25]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 16719446HCID 16719446, compound

Product 1

HCID 86621476HCID 86621476, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Trifluoro-methanesulfonic acid 2-chloro-4-formyl-phenyl ester (I-6a: 10.0 g), 3-cyano-phenyl-boronic acid (5.26 g) and palladium tetrakis(triphenylphosphine) (3.00 g) were combined in 100 mL of dimethoxyethane, then treated with 10 mL of a 2M aqueous sodium carbonate solution before being heated in a 100° C. oil bath. After 24 hours, the reaction mixture was cooled to ambient temperature, the organic phase was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in heptane to afford the title compound (I-6b).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in heptane

Sources & evidence

ORD record
ord-1873f0f8db4644b79af1c76b1ffbb735
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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