Water → HCID 66862833, compound

HRID 1958549Notes

Reaction equation

HRID 1958549 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 66862833HCID 66862833, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-4-(trifluoromethyl)pyridine (4 g, 22.0 mmol), 2-chlorophenylboronic acid (5.04 g, 24.2 mmol), Ba(OH)2 (12.5 g, 66.1 mmol) and Pd(PPh3)2Cl2 (464 mg, 0.66 mmol) in DME (140 mL)/water (35 mL) was heated at 110° C. for 1 h. The solids were filtered off and the mother liquor were concentrated to around 80 mL and extracted with EtOAc. The organic layer was washed with brine, then water, dried (MgSO4), filtered and concentrated. Purification by column chromatography (1/1 Petroleum ether/EtOAc) gave the Suzuki adduct (5.05 g, 89%) as a colourless oil.

Workup

  1. filtrationThe solids were filtered off
  2. concentrationthe mother liquor were concentrated to around 80 mL
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialwater, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography (1/1 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-3337d0237ac644deb7d1b3ab8e5989c5
Source dataset
uspto-grants-2013_04
Patent number
US08410133B2

Reaction notes

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