Acetic Acid → HCID 178506021, compound

HRID 2069576Notes

Reaction equation

HRID 2069576 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C1CCCCO1)[N:6]=[CH:5]2.C(O)(=O)C.[B-](F)(F)(F)[F:22].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(#N)C>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[F:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 2724933SelectfluorHCID 534338265-bromo-1-(oxan-2-yl)-1H-indazole2×

Product 1

HCID 178506021HCID 178506021, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (10.0 g, 35.7 mmol; Intermediate 1), acetic acid (4 mL), Selectfluor (25.3 g, 71.4 mmol), and acetonitrile (100 mL) was refluxed under N2 for 2 h. The reaction was allowed to cool to rt, diluted with ethyl acetate (420 mL), and then washed with water (270 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified on a silica gel column using EtOAc in petroleum ether (1:20) to afford the title compound as yellow solids (6.0 g, yield 78.1%). 1H NMR (DMSO-d6, 400 MHz): δ 12.77 (s, 1H), 7.96 (s, 1H), 7.54 (d, 1H), 7.48 (d, 1H).

Workup

  1. temperaturewas refluxed under N2 for 2 h
  2. washwashed with water (270 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-6c28e8d32ea347228a7abf6d5ea0faa5
Source dataset
uspto-grants-2012_10
Patent number
US08299112B2

Reaction notes

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