Potassium Fluoride → HCID 59443582, compound

HRID 1927683Notes

Reaction equation

HRID 1927683 reaction equation
C[Sn](C)C.C[Sn](C)C.Br[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[N:19]([CH3:29])[C:20]([CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][CH3:26])=[CH:21][N:22]=2)=[CH:12][CH:11]=1.Br[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=1.[F-].[K+]>O1CCOCC1.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>[CH3:27][C:24]([CH3:28])([CH2:25][CH3:26])[CH2:23][C:20]1[N:19]([CH3:29])[C:18]([CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=3)=[CH:11][CH:12]=2)=[N:22][CH:21]=1

Participants

7

Reactant 4

HCID 522689Potassium FluorideHCID 27831712-Bromo-5-fluoropyridineHCID 6327618HexamethylditinHCID 68674592HCID 68674592, compound

Product 1

HCID 59443582HCID 59443582, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Hexamethylditin (174 mg, 0.53 mmol) was added to a solution of 2-[2-(4-bromophenyl)ethyl]-5-(2,2-dimethylbutyl)-1-methyl-1H-imidazole (186 mg, 0.53 mmol), 2-bromo-5-fluoropyridine (94 mg, 0.53 mmol), and tetrakis(triphenylphosphine)palladium (0), (62 mg, 0.053 mmol) in 1,4-dioxane (25 mL). The mixture was stirred overnight at 110° C. KF on Celite (1:1) was added and the solution was stirred at rt for 1 h. The mixture was filtered, and the filtrate was washed with water, dried (MgSO4), filtered, and concentrated in vacuo to give a residue. The residue was purified by flash column chromatography on silica gel eluting with 0-50% EtOAc/hexanes to provide the title compound. LC-MS: m/e 366 (M+H).

Workup

  1. stirringthe solution was stirred at rt for 1 h
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue was purified by flash column chromatography on silica gel eluting with 0-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-3f974cfa76ac461ba03f2b2a884cc5b2
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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