Lithium Chloride → HCID 66627089, compound

HRID 1471243Notes

Reaction equation

HRID 1471243 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH3:16])[N:8]=1)(=O)=O.[Cl-].[Li+].[Br-].[CH3:22][C:23]1[N:28]=[C:27]([Zn+])[CH:26]=[CH:25][CH:24]=1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([C:9]1[N:8]=[C:7]([C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:22])[N:28]=2)[CH:12]=[CH:11][CH:10]=1)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 86619913HCID 86619913, compoundHCID 178426002HCID 178426002, compound

Product 1

HCID 66627089HCID 66627089, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask were added 1.2 g 6-butylpyridin-2-yl trifluoromethanesulfonate, 0.36 g lithium chloride and 10 ml dry tetrahydrofuran. Addition of 12 ml of a 0.5M solution of 6-methyl-2-pyridylzinc bromide in tetrahydrofuran was followed by addition of 242 mg of tetrakis(triphenylphosphine)palladium. The reaction was heated to reflux under nitrogen for 16 hours. The reaction was cooled to 22 C and quenched by adding a solution of 6 g of ethylene diamine tetraacetic acid in 40 ml water pH adjusted to 8 with aqueous sodium bicarbonate. 50 ml Hexane and 20 ml ethyl acetate were added and the mixture was stirred for one hour before the aqueous layer was removed and the organic layer was dried over sodium sulfate. After filtration and solvent removal, the product was purified by silica gel chromatography using 5% ethyl acetate in hexane to give 0.7 g clear colorless oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux under nitrogen for 16 hours
  3. temperatureThe reaction was cooled to 22 C
  4. customquenched
  5. additionby adding a solution of 6 g of ethylene diamine tetraacetic acid in 40 ml water
  6. addition50 ml Hexane and 20 ml ethyl acetate were added
  7. customwas removed
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. filtrationAfter filtration and solvent removal
  10. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-49634aa76e764e5694ee068462352b79
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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