Potassium Carbonate → (S)-tert-butyl 2-(6-(7-bromo-9,10-dihydro-phenanthren-2-yl)-1H-benzo[d]imidazol-2-yl)-pyrrolidine-1-carboxylate

HRID 1751578노트

반응식

HRID 1751578 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([C@@H:17]4[CH2:21][CH2:20][CH2:19][N:18]4[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH:14][C:13]=3[CH:29]=2)O1.[Br:31][C:32]1[CH:45]=[CH:44][C:43]2[C:42]3[C:37](=[CH:38][C:39](Br)=[CH:40][CH:41]=3)[CH2:36][CH2:35][C:34]=2[CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>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.C(COC)OC>[Br:31][C:32]1[CH:33]=[C:34]2[C:43]([C:42]3[CH:41]=[CH:40][C:39]([C:9]4[CH:10]=[CH:11][C:12]5[N:16]=[C:15]([C@@H:17]6[CH2:21][CH2:20][CH2:19][N:18]6[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[NH:14][C:13]=5[CH:29]=4)=[CH:38][C:37]=3[CH2:36][CH2:35]2)=[CH:44][CH:45]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 28250532,7-Dibromo-9,10-dihydrophenanthreneHCID 56605316tert-Butyl (2S)-2-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,3-benzodiazol-2-yl]pyrrolidine-1-carboxylate

생성물 1

HCID 67681965(S)-tert-butyl 2-(6-(7-bromo-9,10-dihydro-phenanthren-2-yl)-1H-benzo[d]imidazol-2-yl)-pyrrolidine-1-carboxylate수율 59.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

A mixture of ((S)-tert-butyl 2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.49 g, 3.6 mmol), 2,7-dibromo-9,10-dihydrophenanthrene (6.09 g, 18.0 mmol), 2M aqueous potassium carbonate solution (9 mL, 18.0 mmol), tetrakis(triphenylphosphine)palladium(0) (209 mg, 0.18 mmol) and dimethoxyethane (36 mL) was degassed with a stream of argon for twenty minutes. The reaction was heated to 85° C. After 16 hours, the reaction was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with saturated aqueous NaHCO3 solution and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash column chromatography to yield (S)-tert-butyl 2-(6-(7-bromo-9,10-dihydro-phenanthren-2-yl)-1H-benzo[d]imidazol-2-yl)-pyrrolidine-1-carboxylate (1.16 g, 59%).

후처리

  1. customwas degassed with a stream of argon for twenty minutes
  2. temperaturethe reaction was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washThe organic phase was washed with saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-882085bd996a4a9f96525320daac98ce
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156823B2

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