4-Fluoroiodobenzene → HCID 117849012, compound

HRID 1477661Notes

Reaction equation

HRID 1477661 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[F:9][C:10]1([F:24])[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][NH:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[F:24][C:10]1([F:9])[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:14][CH2:13][N:12]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11]1

Participants

7

Reactant 4

HCID 96054-FluoroiodobenzeneHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 56924440tert-Butyl 6,6-difluoro-1,4-diazepane-1-carboxylate

Product 1

HCID 117849012HCID 117849012, compoundYield 11.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1140TolueneSolvent

Procedure

To a toluene solution (2.0 mL) of 1-fluoro-4-iodobenzene (62.6 mg, 0.282 mmol), tert-butyl 6,6-difluoro-1,4-diazepane-1-carboxylate (100 mg, 0.423 mmol), cesium carbonate (184 mg, 0.564 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (23.3 mg, 0.0423 mmol), and palladium acetate (II) (6.30 mg, 0.0282 mmol) were added and the resultant mixture was stirred under nitrogen atmosphere at 110° C. for 4 hours. After completion of the reaction, the reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain a compound (10.2 mg, yield 11%) in Reference Synthesis Example 260 and a compound (6.30 mg, yield 7%) in Reference Synthesis Example 261 as the title compounds.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-5bc75a0e3912436c93ac48fe1d1a7ed8
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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