Ethyl Acetate → HCID 68679989, 화합물

HRID 1869349노트

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HRID 1869349 반응식
[F:1][C:2]([F:30])([F:29])[C:3]([CH:18]=[N:19][C:20]1[CH:28]=[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]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]2[C:13]=1[CH:18]([NH:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=1[CH:22]=[N:23][NH:24]3)[C:3]([C:2]([F:29])([F:1])[F:30])([OH:17])[CH2:4][C:5]2([CH3:7])[CH3:6]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 17989271HCID 17989271, 화합물

생성물 1

HCID 68679989HCID 68679989, 화합물수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-30 °C

실험 절차

100 mg (0.206 mmol) of 1,1,1-trifluoro-4-(5-bromo-2-methoxyphenyl)-2-[(1H-indazol-4-yl)iminomethyl]-4-methylpentan-2-ol is dissolved in one milliliter of dichloromethane, and the reaction mixture is cooled to −30° C. Four milliliters of a 1 M solution of BBr3 in dichloromethane is added in drops within 15 minutes, and the batch is then stirred for 45 more minutes at −30° C. At −30° C., about 10 ml of a saturated sodium bicarbonate solution is carefully added in drops. After dilution with ethyl acetate, it is stirred for ten minutes and then extracted twice with 50 ml each of ethyl acetate. The combined organic extracts are washed with water and brine. The residue that is obtained after the solvent is dried and spun off is chromatographed several times on silica gel (mobile solvent ethyl acetate/dichloromethane). 21 mg of the desired compound (together with the corresponding Desbrom compound) is isolated.

후처리

  1. extractionextracted twice with 50 ml each of ethyl acetate
  2. washThe combined organic extracts are washed with water and brine
  3. customThe residue that is obtained after the solvent
  4. customis dried
  5. customis chromatographed several times on silica gel (mobile solvent ethyl acetate/dichloromethane)

출처 및 근거

ORD 기록
ord-7a552734060e4d66b4805cde074b3d4b
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638515B2

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