Lithium Chloride → HCID 21956523, compound

HRID 2213098Notes

Reaction equation

HRID 2213098 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.FC(F)(F)S(O[C:26]1[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][C:27]=1[O:34][CH3:35])(=O)=O.[Cl-].[Li+]>CN(C=O)C.C(OCC)C.O.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>[CH3:35][O:34][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][C:26]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[C:32]#[N:33]

Participants

8

Reactant 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 166592584-Cyano-2-methoxyphenyl trifluoromethanesulfonate

Product 1

HCID 21956523HCID 21956523, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-(tributylstannyl)pyridine (18 g of 80% pure, 39.2 mmol) and 4-cyano-2-methoxyphenyl trifluoromethanesulfonate (9.2 g, 32.7 mmol) were dissolved in DMF (65 mL) and treated with lithium chloride (1.39 g, 32.7 mmol) and Pd(PPh3)4 (1.9 g, 1.6 mmol), then degassed by bubbling argon through the solution for 15 min. The reaction mixture was heated to 100° C. while under an atmosphere of argon for 12 h. The cooled reaction mixture was diluted with diethyl ether (100 mL) and water (100 mL). The organic layer was separated and washed with a 1M solution of sodium hydroxide (50 mL) and brine (50 mL), then dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1) to afford 3-methyoxy-4-pyridin-2-ylbenzonitrile.

Workup

  1. customdegassed
  2. customby bubbling argon through the solution for 15 min
  3. customThe cooled reaction mixture
  4. customThe organic layer was separated
  5. washwashed with a 1M solution of sodium hydroxide (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1)

Sources & evidence

ORD record
ord-6f58c5203533400ebf11ac98e78b3bd2
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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