Acetone → HCID 66767284, compound

HRID 1662004Notes

Reaction equation

HRID 1662004 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10](C1CCCCO1)[N:9]=[CH:8]2.FC(F)(F)C(O)=O.CC(C)=O>C(Cl)Cl>[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:10][N:9]=[CH:8]2

Participants

5

Reactant 3

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 66767080HCID 66767080, compound

Product 1

HCID 66767284HCID 66767284, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-6-carboxylate (15 g, 35 mmol) in DCM (300 mL) is added trifluoroacetic acid (TFA) (30 mL), and stirred at RT overnight. DCM is evaporated. The residue is partitioned between EtOAc (800 mL) and 5% aqueous NaHCO3 (400 mL). The organic layer is washed with saturated aqueous sodium chloride, dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography eluting with PE:acetone (5:1) to afford the product (10.4 g, 86% yield). MS (m/z): 346.1 (M+H).

Workup

  1. customDCM is evaporated
  2. customThe residue is partitioned between EtOAc (800 mL) and 5% aqueous NaHCO3 (400 mL)
  3. washThe organic layer is washed with saturated aqueous sodium chloride
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography
  7. washeluting with PE

Sources & evidence

ORD record
ord-14aa15675f5a4a6f9544c25e1b9ded09
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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