Selectfluor → HCID 59756548, compound

HRID 2405753Notes

Reaction equation

HRID 2405753 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH2:13])=[C:9]([Cl:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[B-](F)(F)(F)[F:15].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([F:15])[C:8]([NH2:13])=[C:9]([Cl:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 59756561HCID 59756561, compound

Product 1

HCID 59756548HCID 59756548, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.62 g (12.3 mmol) of 1,7-dichloro-isoquinolin-6-ylamine in DMF (130 mL) was added 5.5 g (15.5 mmol) of Selectfluor® as a solid in one portion. The mixture was stirred at room temperature for 15 h. The mixture was poured over ice and stirred until all of the ice had melted during which time a solid precipitated from solution. The brown solid was collected by filtration, washed with water and dried on the filter pad to provide 1.0 g (60% by 1H-NMR, 21%) of 1,7-dichloro-5-fluoro-isoquinolin-6-ylamine. MS calc. for C9H5Cl2FN2 [M]+: 231.05. Found: 231.68.

Workup

  1. additionThe mixture was poured over ice
  2. customprecipitated from solution
  3. filtrationThe brown solid was collected by filtration
  4. washwashed with water
  5. customdried on the filter pad

Sources & evidence

ORD record
ord-85fb4fcfdcfc4ec6a7d98ffe89c7c0b0
Source dataset
uspto-grants-2014_08
Patent number
US08809326B2

Reaction notes

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