Cornforth reagent → HCID 76846386, compound

HRID 1615261Notes

Reaction equation

HRID 1615261 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 68753043HCID 68753043, compound

Product 1

HCID 76846386HCID 76846386, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (4-chloro-1H-indazol-6-yl)methanol (30 mg, 0.18 mmol) in acetone (5 mL) was added PDC (100 mg, 0.27 mmol). The mixture was stirred overnight at rt. The mixture was filtered through celite, the filter cake was washed with ethyl acetate. The solution was washed with water (2×10 mL), brine (10 mL), dried over MgSO4 and concentrated to a brown solid (30 mg, 100%). 1H NMR (400 MHz, CD3OD) δ 10.1 (s, 1H), 8.21 (s, 1H), 8.08 (s, 1H), 7.62 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake was washed with ethyl acetate
  3. washThe solution was washed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to a brown solid (30 mg, 100%)

Sources & evidence

ORD record
ord-18b8bd29a97046fc80a7b72fcadc9f15
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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