Potassium Fluoride → 4-(4-Chloro-2-methylphenyl)-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

HRID 1472772Notes

Reaction equation

HRID 1472772 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:18]#[N:19])[S:5][C:6]=1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[CH:9][CH:8]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[C:23]([CH3:30])[CH:22]=1.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:3]=[C:4]([C:18]#[N:19])[S:5][C:6]=2[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[CH:9][CH:8]=2)=[C:23]([CH3:30])[CH:22]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 682936224-Bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

Product 1

HCID 682936984-(4-Chloro-2-methylphenyl)-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrileYield 90.6%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

A round-bottomed flask was charged with 4-bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile (203 mg, 0.62 mmol), 4-chloro-2-methylphenylboronic acid (119 mg, 0.70 mmol), Pd2(dba)3 (9.2 mg, 0.010 mmol) and KF (126 mg, 2.17). After degassed, dioxane (2.0 mL) and P(Bu-t)3 (0.15 mL, 0.2M, 0.03 mmol) was added. The reaction mixture was stirred at rt until complete. 20 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:CH2Cl2=3:1). 0.21 g (90.6%) of product was obtained as a white solid.

Workup

  1. customAfter degassed
  2. additiondioxane (2.0 mL) and P(Bu-t)3 (0.15 mL, 0.2M, 0.03 mmol) was added
  3. addition20 mL of water was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (hexane:CH2Cl2=3:1)

Sources & evidence

ORD record
ord-cad9fe2fa4a04c468171590c5702b5e0
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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