Potassium Carbonate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(5-methoxypyridin-3-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol

HRID 879280노트

반응식

HRID 879280 반응식
C([O:7][CH2:8][C@@H:9]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)(=O)C(C)(C)C.[CH3:46][O:47][C:48]1[CH:49]=[N:50][CH:51]=[C:52](B2OC(C)(C)C(C)(C)O2)[CH:53]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[C:42]([O:41][C@@H:9]([C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:52]4[CH:51]=[N:50][CH:49]=[C:48]([O:47][CH3:46])[CH:53]=4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[CH2:8][OH:7])([CH3:43])([CH3:44])[CH3:45]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86699797(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy)phenyl)benzo[d]thiazol-6-yl)ethyl pivalate

생성물 1

HCID 86699796(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(5-methoxypyridin-3-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol수율 62%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

The reaction mixture of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy) phenyl)benzo[d]thiazol-6-yl)ethyl pivalate (20 mg, 0.029 mmol), 3-methoxypyridine-5-boronic acid pinacol ester (10 mg, 0.043 mmol), 2N K2CO3 (70 μL), Pd(PPh3)4 (3.3 mg, 0.0029 mmol) in dioxane (1 mL) was heated at 120° C. in sealed tube for 2 hours. After the reaction finished, the reaction was cooled down, to the reaction mixture was added MeOH (1 mL), 2N NaOH (500 μL) and heated at 45° C. for 3 hours. Then reaction mixture was washed by sat. NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product (10 mg, 62%). LCMS-ESI+: calc'd for C32H31ClN2O3S: 559.2 (M+H+); Found: 559.2 (M+H+).

후처리

  1. temperaturethe reaction was cooled down, to the reaction mixture
  2. temperatureheated at 45° C. for 3 hours
  3. customThen reaction mixture
  4. washwas washed by sat. NaHCO3
  5. extractionextracted by EtOAc
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated down
  9. custompurified by silica gel column
  10. washeluting by 0-100% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-51759c0b0a0f43189e3204a261f07c8c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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