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 1444490노트

반응식

HRID 1444490 반응식
[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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d1b5e02f9bae49d3b6ec56149838ce6d
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662821B2

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