Dichloromethane → HCID 24730073, compound

HRID 1486979Notes

Reaction equation

HRID 1486979 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[C:19]1[N:24]=[C:23]([CH:25]=[O:26])[CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].ClCCl>COCCOC.O.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(OCC)(=O)C.CCCCCC>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:19]2[N:24]=[C:23]([CH:25]=[O:26])[CH:22]=[CH:21][CH:20]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 24730073HCID 24730073, compoundYield 48.8%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In a 35 mL, microwave vial, 3,5-bis(trifluoromethyl)phenylboronic acid (2.0 g, 7.7 mmol) and 6-bromopicolinaldehyde (1a) (1.44 g, 7.7 mmol) dissolved in 1,2-dimethoxyethane (20 mL) was treated with a solution of K2CO3 (3.22 g, 23.3 mmol) in water at room temperature. Pd(dppf)Cl2.dichloromethane was added to reaction mass and charged in microwave for 30 min at 90° C. The progress of the reaction was monitored by TLC analysis on silica gel with ethyl acetate:hexane (3:7) as mobile phase. Reaction mixture was poured into water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine solution (3×50 mL), dried over MgSO4, filtered, and concentrated by rotary evaporation to afford 2.5 g of Crude compound which was purified by chromatography. Product elute at 4% ethyl acetate in hexane to give 1.2 g of pure product. (Yield 48.38%).

Workup

  1. additioncharged in microwave for 30 min at 90° C
  2. customReaction mixture
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined organic layers were washed with brine solution (3×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customto afford 2.5 g of Crude compound which
  9. customwas purified by chromatography
  10. washProduct elute at 4% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a7662bb8ee46419e8da0c62786bbab09
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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