Cesium fluoride → HCID 59003117, compound

HRID 2353886Notes

Reaction equation

HRID 2353886 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]([C:31](=[O:33])[CH3:32])[CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C:10]2[CH:34]=[CH:35][C:36](Br)=[CH:37][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:39]B(O)O.[F-].[Cs+]>O1CCOCC1.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]([C:31](=[O:33])[CH3:32])[CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C:10]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 139377Methylboronic AcidHCID 59003137HCID 59003137, compound

Product 1

HCID 59003117HCID 59003117, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Combine tert-butyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.438 g, 0.719 mmol), methylboronic acid (0.086 g, 1.44 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.059 g, 0.072 mmol) and cesium fluoride (0.328 g, 2.16 mmol) in dioxane (2.5 mL) in a 10 mL microwave vessel and irradiate this mixture at 110° C. for 80 min. Dilute the cooled mixture with dichloromethane and filter through Celite®. Remove the filtrate solvent under reduced pressure and purify the residue first using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to afford the title compound as a white solid (0.116 g, 30%).

Workup

  1. filtrationfilter through Celite®
  2. customRemove the filtrate solvent under reduced pressure
  3. custompurify the residue
  4. washeluting with hexanes/ethyl acetate (60:40)

Sources & evidence

ORD record
ord-83dc937d3d2f48e7abef92556acd5ca4
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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