2-Bromo-5-fluoropyridine → HCID 66705671, compound

HRID 425350Notes

Reaction equation

HRID 425350 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][C:4]1[N:5]=[C:6]([C:15]([OH:29])(C)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Sn](C)(C)C)=[CH:19][C:18]=2[F:27])[N:7]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:8]=1.Br[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=1>O1CCOCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:31][C:2]([CH3:30])([CH3:1])[CH2:3][C:4]1[N:5]=[C:6]([C:15](=[O:29])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=3)=[CH:19][C:18]=2[F:27])[N:7]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:8]=1

Participants

6

Reactant 2

HCID 27831712-Bromo-5-fluoropyridineHCID 66705660HCID 66705660, compound

Product 1

HCID 66705671HCID 66705671, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Palladium tetrakis(triphenylphosphine) (42 mg, 0.04 mmol) was added to a degassed, ambient temperature solution of 4-(2,2-dimethylpropyl)-2-{2-[2-fluoro-4-(trimethylstannyl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (200 mg, 0.37 mmol) and 2-bromo-5-fluoropyridine (129 mg, 0.74 mmol) in 1,4-dioxane (5 mL). After stirring at reflux overnight, the reaction mixture was diluted with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-40% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-{[2-fluoro-4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with methylene chloride and ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-648cd4820f314fbd97352b353889633a
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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