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 1751578Notes

Reaction equation

HRID 1751578 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-882085bd996a4a9f96525320daac98ce
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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