Lithium Hydroxide → HCID 66766833, compound

HRID 1661991Notes

Reaction equation

HRID 1661991 reaction equation
C([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:8][C:7]=1[O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=1[F:31])=[O:5])C.[Li+].[OH-].CCOC(C)=O.C(O)(=O)C>C1COCC1.CO.O>[F:31][C:23]1[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=[CH:27][C:22]=1[O:21][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:6]=1[C:4]([OH:5])=[O:3])[N:12]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[N:11]=[CH:10]2

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 22609514Ethyl acetate acetateHCID 66767080HCID 66767080, compound

Product 1

HCID 66766833HCID 66766833, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-6-carboxylate (22 g, 51.2 mmol) in THF (60 mL) and MeOH (60 mL) and H2O (10 mL) is added LiOH (3 g, 125 mmol). The resulting solution is stirred at RT for 1.5 hours and the organic solvents are removed. The aqueous residue is acidified with cold 6N HCl to pH 2, and extracted with EtOAc (150 mL). The organic phase is separated, dried, and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc:acetic acid (100:100:1) to afford the product (19.5 g, 95% yield). MS (m/z): 402.1 (M+H).

Workup

  1. customthe organic solvents are removed
  2. extractionextracted with EtOAc (150 mL)
  3. customThe organic phase is separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography
  7. washeluting with PE

Sources & evidence

ORD record
ord-b62036b752f2459793756f3f0c69b16e
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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