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 1751578ノート

反応式

HRID 1751578 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-882085bd996a4a9f96525320daac98ce
出典データセット
uspto-grants-2015_10
特許番号
US09156823B2

反応ノート

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