Ethyl Acetate → 1-(5-Methyl-1H-indazol-4-ylamino)-6-fluoro-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydro-naphthalene-2,5-diol

HRID 1443222Notes

Reaction equation

HRID 1443222 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([CH:18]=[N:19][C:20]1[C:28]([CH3:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[N:23][NH:24]2)([OH:17])[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[O:15]C)([CH3:7])[CH3:6].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl>[CH3:29][C:28]1[C:20]([NH:19][CH:18]2[C:13]3[CH:12]=[CH:11][C:10]([F:14])=[C:9]([OH:15])[C:8]=3[C:5]([CH3:6])([CH3:7])[CH2:4][C:3]2([C:2]([F:31])([F:30])[F:1])[OH:17])=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][N:23]=[CH:22]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 686820761,1,1-Trifluoro-4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methyl-1H-indazol-4-ylimino)-methyl]-pentan-2-ol

Product 1

HCID 865999241-(5-Methyl-1H-indazol-4-ylamino)-6-fluoro-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydro-naphthalene-2,5-diol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Trifluoro-4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methyl-1H-indazol-4-ylimino)-methyl]-pentan-2-ol (150 mg, 0.34 mmol) is mixed with boron tribromide (3.40 ml of a 1 M solution in dichloromethane, 3.4 mmol) at room temperature. After 4 hours at room temperature, the reaction mixture is allowed to stand overnight at −30° C., then saturated sodium bicarbonate solution and ethyl acetate are added. It is extracted with ethyl acetate, and the combined organic phases are washed with saturated sodium chloride solution and dried on sodium sulfate. After the solvent is removed in a vacuum as well as purification by means of preparative thin-layer chromatography on silica gel with hexane/ethyl acetate (50% ethyl acetate), 56 mg (39% of theory) of the product is obtained.

Workup

  1. waitto stand overnight at −30° C.
  2. extractionIt is extracted with ethyl acetate
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. customAfter the solvent is removed in a vacuum as
  6. customwell as purification by means of preparative thin-layer chromatography on silica gel with hexane/ethyl acetate (50% ethyl acetate), 56 mg (39% of theory) of the product
  7. customis obtained

Sources & evidence

ORD record
ord-c891e3b8b8114c2db0ad92a3e8c6cd1e
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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