Tetrahydrofuran → HCID 178509929, compound

HRID 505509Notes

Reaction equation

HRID 505509 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)[CH:9]=1)[C:5]#[N:6].CC([O-])(C)C.[K+].C1COCC1.[Cl:32]N1C(=O)CCC1=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]3[C:12]=2[C:13]([Cl:32])=[N:14][NH:15]3)[CH:9]=1)[C:5]#[N:6]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 31398ChlorosuccinimideHCID 23665647Potassium tert-butoxideHCID 568336433-chloro-5-[(5-chloro-1H-indazol-4-yl)oxy]benzonitrile

Product 1

HCID 178509929HCID 178509929, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-5-[(5-chloro-1H-indazol-4-yl)oxy]benzonitrile (100 mg, 0.329 mmol) in DMF (1 mL) was added 1.0M KOtBu in THF (329 μL, 0.329 mmol) and then N-chlorosuccinimide (44 mg, 0.329 mmol). The resulting reaction mixture was then stirred for 10 minutes, after which the mixture was purified on a LUNA column (10μ, C18, 250×21.2 cm) eluting with 5-95% ACN/water with 0.1% TFA) to give the title compound.

Workup

  1. customThe resulting reaction mixture
  2. customafter which the mixture was purified on a LUNA column (10μ, C18, 250×21.2 cm)
  3. washeluting with 5-95% ACN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-0b1d60585c504afa8b7ecbc28ce96b33
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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