Hydrogen Peroxide → 1-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-ethane-1,2-diol

HRID 32023노트

반응식

HRID 32023 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH:19]([OH:28])[CH2:20][Si](OC(C)C)(C)C)=[CH:11][C:12]3[NH:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([Cl:29])[CH:3]=1.[F-].[K+].[OH:32]O>CO.C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH:19]([OH:28])[CH2:20][OH:32])=[CH:11][C:12]3[NH:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([Cl:29])[CH:3]=1

참가 물질

6

반응물 3

HCID 784Hydrogen PeroxideHCID 522689Potassium FluorideHCID 211141671-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-(isopropoxy-dimethyl-silanyl)-ethanol

생성물 1

HCID 211141701-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-ethane-1,2-diol수율 34%

시약·촉매·용매 2

HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To the crude 1-[6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-(isopropoxy-dimethyl-silanyl)-ethanol 10v in MeOH-THF (5 mL-5 mL) is added KHCO3 (54 mg, 0.54 mmol), and KF (74 mg, 1.27 mmol), and 30% aqueous H2O2 (0.20 mL) at room temperature. After stirring for 3.5 hours at room temperature, the reaction mixture is diluted with water, and extracted with EtOAc. The organic layer is dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography (8% to 10% MeOH in CH2Cl2) to give the desired product (74 mg, 34%): MS APCI (+) m/z 400, 402 (M+, Br pattern) detected; 1H NMR (400 MHz, CD3OD) δ 8.20 (s, 1H), 7.62 (broad s, 1H), 7.47 (d, 1H), 7.14 (dd, 1H), 6.30 (d, 1H), 4.96 (t, 1H), 3.64 (m, 2H); 19F NMR (376 MHz, CD3OD) −136.87 (s).

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (8% to 10% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-b7d27793b5db463d97d2a8a9f364b602
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425637B2

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