Selectfluor → HCID 59519505, compound

HRID 1161809Notes

Reaction equation

HRID 1161809 reaction equation
[NH2:1][C:2]1[C:11](Cl)=[C:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[B-](F)(F)(F)[F:23].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CO.O.CCOC(C)=O>[NH2:1][C:2]1[C:11]([F:23])=[C:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 59519414HCID 59519414, compound

Product 1

HCID 59519505HCID 59519505, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of methyl 6-amino-5-chloro-4-(2-fluoro-4-iodophenylamino)nicotinate (2.0 g, 4.74 mmol) (Example 11, step E) in a mixture of MeOH/water (1/1) (20 ml) is added selectfluor (1.6 g, 4.74 mmol). The mixture is stirred at room temperature overnight, diluted with EtOAc and washed with 0.5 N HCl and brine. The organic extracts are dried (Na2SO4) and concentrated under reduced pressure. The crude material was purified by HPLC (reverse phase) to obtain the title compound.

Workup

  1. washwashed with 0.5 N HCl and brine
  2. dry with materialThe organic extracts are dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by HPLC (reverse phase)

Sources & evidence

ORD record
ord-1d151c46245a47caba09dd19ef478972
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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