Sodium Carbonate → HCID 87782654, compound

HRID 2219816Notes

Reaction equation

HRID 2219816 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[N:11][OH:12])[CH2:6][CH2:5]2.[C:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.[Pd].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>[OH:12]/[N:11]=[C:7]1\[CH2:6][CH2:5][C:4]2[C:8]\1=[CH:9][CH:10]=[C:2]([C:19]1[CH:20]=[C:15]([CH:16]=[CH:17][CH:18]=1)[C:13]#[N:14])[CH:3]=2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 72292220HCID 72292220, compound

Product 1

HCID 87782654HCID 87782654, compoundYield 43.9%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 5-bromoindan-1-one oxime (0.25 g, 1.10 mmol) in glyme (11 mL) was added 3-cyanophenyl boronic acid (0.21 g, 1.44 mmol), sodium carbonate (0.35 g, 3.30 mmol) dissolved in deionized (D.I.) water (2 mL), and tetrakis(triphenylphosphine) palladium (0) (0.06 g, 0.05 mmol). The resulting solution was heated to reflux for 2 hours. The solution was cooled to room temperature and partitioned between ammonium chloride solution (sat.) and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (20% ethyl acetate/hexane) and triturated with ether to give 3-[(1E)-1-(hydroxyimino)-2,3-dihydro-1H-inden-5-yl]benzonitrile as a white solid (0.12 g, 43%). MS (ESI) m/z 249; HRMS: calcd for C16H12N2O+H+, 249.10224; found (ESI, [M+H]+), 249.1033.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 2 hours
  3. custompartitioned between ammonium chloride solution (sat.) and ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column (20% ethyl acetate/hexane)
  8. customtriturated with ether

Sources & evidence

ORD record
ord-f13c6ee4ebc04a5cad6f0743677856df
Source dataset
uspto-grants-2008_08
Patent number
US07414142B2

Reaction notes

Loading…