Potassium Fluoride → HCID 68293606, compound

HRID 1472781Notes

Reaction equation

HRID 1472781 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[S:11][C:10]([C:12]#[N:13])=[CH:9][C:8]=2I)=[CH:4][CH:3]=1.[CH3:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](B(O)O)=[CH:20][CH:19]=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:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[S:11][C:10]([C:12]#[N:13])=[CH:9][C:8]=2[C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]([CH3:17])=[CH:19][CH:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 68293620HCID 68293620, compound

Product 1

HCID 68293606HCID 68293606, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

A round-bottomed flask was charged with 5-(4-chlorobenzyl)-4-iodothiophene-2-carbonitrile (180 mg, 0.50 mmol), 4-methylnaphthalen-1-ylboronic acid (102 mg, 0.55 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 (5% ethyl acetate in hexane). 0.17 g (91%) 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 (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-448f40b3a311422dbcba69140e35e412
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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