Potassium Carbonate → 2-(4-(Quinolin-7-yl)phenyl)acetonitrile

HRID 1525868Notes

Reaction equation

HRID 1525868 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[CH:24][CH:25]=[N:26]3)=[CH:21][CH:20]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[N:26]1[C:27]2[C:22](=[CH:21][CH:20]=[C:19]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=3)[CH:28]=2)[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27914Benzeneacetonitrile, 4-bromo-HCID 592961167-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Quinoline

Product 1

HCID 712709262-(4-(Quinolin-7-yl)phenyl)acetonitrileYield 68.1%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(4-bromophenyl)acetonitrile (2.55 mmol) in 1,4-dioxane (5 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (2.64 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.083 mmol), and 2M aq potassium carbonate (5.10 mmol). The reaction vessel was purged with nitrogen and sealed, and the mixture irradiated in a Biotage Initiator Microwave at 120° C. for 20 min. The resulting black mixture was diluted with water (100 mL) and extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-100% ethyl acetate/hexanes) afforded the title compound as a yellow solid (424 mg, 64%). MS(ES)+ m/e 245.3 [M+H]+.

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. customsealed
  3. customthe mixture irradiated in a Biotage Initiator Microwave at 120° C. for 20 min
  4. additionThe resulting black mixture was diluted with water (100 mL)
  5. extractionextracted three times with dichloromethane
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-85c2084202434537b52b323faa031d87
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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