Sodium Carbonate → 2',6-Dichloro-4-vinyl-[1,1'-biphenyl]-3-amine

HRID 588804Notes

Reaction equation

HRID 588804 reaction equation
Br[C:2]1[C:3]([Cl:11])=[CH:4][C:5]([CH:9]=[CH2:10])=[C:6]([NH2:8])[CH:7]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[C:3]([Cl:11])=[CH:4][C:5]([CH:9]=[CH2:10])=[C:6]([NH2:8])[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 1176071655-Bromo-4-chloro-2-vinylbenzenamine

Product 1

HCID 904603862',6-Dichloro-4-vinyl-[1,1'-biphenyl]-3-amineYield 73.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-4-chloro-2-vinylbenzenamine (600 mg, 2.6 mmol), 2-chlorophenylboronic acid (1.25 g, 12.9 mmol), Pd(PPh3)4 (300 mg, 0.2 6 mmol), Na2CO3 (1.4 g, 13.0 mmol) in 1,4-dioxane (20 mL) and water (5 mL) was stirred at reflux under argon for 16 h. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30:1) to afford the desired product (500 mg, 73.1% yield). ESI-MS m/z: 263.1[M+H]+.

Workup

  1. temperatureat reflux under argon for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30:1)

Sources & evidence

ORD record
ord-344f197f21054b179b7be94fe86e1664
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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