Cesium fluoride → HCID 58975170, compound

HRID 1178976Notes

Reaction equation

HRID 1178976 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][NH:7][C:8](=[O:36])[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](B4OC(C)(C)C(C)(C)O4)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Br[C:40]1[CH:41]=[CH:42][C:43]([F:46])=[N:44][CH:45]=1.[F-].[Cs+]>CN(C=O)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>[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][NH:7][C:8](=[O:36])[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:40]4[CH:45]=[N:44][C:43]([F:46])=[CH:42][CH:41]=4)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27831685-Bromo-2-fluoropyridineHCID 58975028N-[(4-Fluorophenyl)methyl]-4-[[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl]sulfonyl]benzamide

Product 1

HCID 58975170HCID 58975170, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combine N-(4-Fluoro-benzyl)-4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-sulfonyl]-benzamide (150 mg, 0.28 mmol), 5-Bromo-2-fluoro-pyridine (0.05 mL, 0.56 mmol), CsF (212 mg, 1.4 mmol) and Pd(Ph3P)4 (32 mg, 0.028 mmol) in 1.0 mL DMF and 0.100 mL of water. Evacuate the reaction vessel and place under an atmosphere of nitrogen. Heat the resulting reaction at 90 degrees 12 h. Load the reaction directly onto silica gel and purify by flash column chromatography (EtOAc/Hexanes) to yield 98 mg of white foam (70%) LRMS: MH+ 504.02.

Workup

  1. customEvacuate the reaction vessel and place under an atmosphere of nitrogen
  2. temperatureHeat
  3. customthe resulting reaction at 90 degrees 12 h
  4. customLoad the reaction directly onto silica gel
  5. custompurify by flash column chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-f6d45e677a0f4a94ac3bff138b7cc3dd
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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