Methanol → (S)-2-(2-(3-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol

HRID 879284노트

반응식

HRID 879284 반응식
C([O:7][CH2:8][C@H:9]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20](Br)[S:21][C:17]=2[C:16]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=O)C(C)(C)C.[Br:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1.CO.[OH-].[Na+]>O1CCOCC1>[Br:33][C:34]1[CH:35]=[C:36]([C:20]2[S:21][C:17]3[C:16]([C:26]4[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=4)=[C:15]([C@H:9]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:8][OH:7])[C:24]([CH3:25])=[CH:23][C:18]=3[N:19]=2)[CH:37]=[CH:38][CH:39]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2734318(3-Bromophenyl)boronic acidHCID 86699799(S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

생성물 1

HCID 86699802(S)-2-(2-(3-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol수율 36%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a solution of (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (310 mg, 0.577 mmol) in dioxane (5 mL), was added 3-bromophenylboronic acid (173 mg, 0.865 mmol), Ph(PPh3)4 (33 mg, 0.029 mmol) 2N K2CO3 (850 μL) in sealed tube. The reaction mixture was heated at 90° C. for 3hs. Then the reaction was cooled down and to the mixture was added MeOH (5 mL), 2N NaOH (1.5 mL) and heated at 45° C. After the reaction was finished, the reaction was washed by water, extracted by EtOAc. The organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-50% EtOAc in hexanes to give the product (110 mg, 36%). LCMS-ESI+: calc'd for C26H25BrClNO2S: 530.0 (M+H+); Found: 530.2 (M+H+).

후처리

  1. temperatureThen the reaction was cooled down and to the mixture
  2. temperatureheated at 45° C
  3. washthe reaction was washed by water
  4. extractionextracted by EtOAc
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. custompurified by silica gel column
  9. washeluting by 0-50% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-af4ee16cc3d6404e874483577796ab0a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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