Cesium fluoride → N-(4-Fluoro-benzyl)-4-[3-(2-fluoro-pyridin-3-yl)-indole-1-sulfonyl]-benzamide

HRID 737044Notes

Reaction equation

HRID 737044 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](I)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[F-:31].[Cs+].O1[CH2:38][CH2:37]OCC1>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:5]4[C:6]([F:31])=[N:7][CH:8]=[CH:37][CH:38]=4)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 58975061N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide

Product 1

HCID 57849040N-(4-Fluoro-benzyl)-4-[3-(2-fluoro-pyridin-3-yl)-indole-1-sulfonyl]-benzamideYield 50%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

Combine N-(4-Fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (300 mg, 0.56 mmol), 2-Fluoro-3-boronic acid-pyridine (140 mg, 1.12 mmol), CsF (170 mg, 1.12 mmol) and Dichlorobis(triphenylphosphine)palladium (100 mg, 0.14 mmol) in dioxane (2.0 mL) and water (0.200 mL). Evacuate the reaction and place under a nitrogen atmosphere. Heat the resulting reaction in an 80 degree oil bath for 15 h. Cool the reaction and filter through a short pad of silica gel with additional ethyl acetate. Evaporate and purify by flash column chromatography (EtOAc/Hexanes) to yield 141 mg of an off white foam (50%) LRMS: MH+ 503.92.

Workup

  1. customEvacuate
  2. customthe reaction and place under a nitrogen atmosphere
  3. temperatureHeat
  4. customthe resulting reaction in an 80 degree oil bath for 15 h
  5. temperatureCool
  6. customthe reaction
  7. filtrationfilter through a short pad of silica gel with additional ethyl acetate
  8. customEvaporate
  9. custompurify by flash column chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-460bc203acaf4d93b6914fec75afef83
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…