Selectfluor → 1-(4-chloro-2-trifluoromethyl-benzyl)-3-fluoro-1H-indazole-5-carbaldehyde

HRID 2400968Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=1.[B-](F)(F)(F)[F:25].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=3)[C:9]([F:25])=[N:8]2)=[C:4]([C:20]([F:22])([F:23])[F:21])[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A suspension of 1-[4-Chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-carbaldehyde (0.9 mmol, from Example 1)) and SelectFluor® (2 eq., Aldrich) in CH3CN (3 mL) was heated in a microwave reactor at 140° C. for 30 min. The solvent was evaporated and the residue was washed with DCM. The insoluble solid was discarded. The combined organic washings were concentrated and the residue was purified by flash chromatography (0-20% EtOAc/Hex) to afford 1-[4-chloro-2-(trifluoromethyl)benzyl]-3-fluoro-1H-indazol-5-carbaldehyde.

Workup

customThe solvent was evaporated
washthe residue was washed with DCM
concentrationThe combined organic washings were concentrated
customthe residue was purified by flash chromatography (0-20% EtOAc/Hex)

Sources & evidence

ORD record: ord-c4f14e175b9042ee9f8c66e6293ca043
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796256B2

Reaction notes

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