Water → HCID 67056312, compound

HRID 1777279Notes

Reaction equation

HRID 1777279 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.O>C1(C)C=CC=CC=1.Cl.Cl.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 67056312HCID 67056312, compoundYield 9,083%

Reagents, catalysts & solvents 2

HCID 178478646HCID 178478646, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

16.5 ml (0.3 mmol) of an aqueous solution of potassium carbonate having a concentration of 2M and 0.4 g (0.1 mmol) of 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dihydrochloride are added under a stream of nitrogen to a solution containing 2.0 g (0.1 mmol) of 2-bromopyridine-4-methanol and 2.2 g (0.1 mmol) of 2-(trifluoromethyl)phenylboronic acid in 30 ml of toluene. The mixture is stirred at 80° C. for 5 hours then 20 ml of water are added. After extraction with ethyl acetate, the organic phase is dried over sodium sulphate, filtered and evaporated. The residue obtained is purified by chromatography over silica gel eluted with a 60/40 heptane/ethyl acetate mixture. 2.3 g (85%) of [2-(2-trifluoromethylphenyl)pyridin-4-yl]methanol are obtained in the form of a yellow oil.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography over silica gel
  7. washeluted with a 60/40 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c8262577d30347f2937d22dafb51060b
Source dataset
uspto-grants-2016_02
Patent number
US09266848B2

Reaction notes

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