Sodium Carbonate → HCID 58488519, 화합물

HRID 451358노트

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HRID 451358 반응식
Br[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH3:11].[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=2[CH3:11])=[C:15]([C:22]([F:23])([F:24])[F:25])[CH:14]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 121094694-Fluoro-2-(trifluoromethyl)benzeneboronic acidHCID 66924763Methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate

생성물 1

HCID 58488519HCID 58488519, 화합물수율 62%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매HCID 22272177Toluene water용매

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온도
110 °C

실험 절차

A mixture of methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (0.27 g, 1.2 mmol), [4-fluoro-2-(trifluoromethyl)phenyl]boronic acid (0.61 g, 2.9 mmol), Na2CO3 (0.6 g, 5.7 mmol) and palladium tetrakis(triphenylphosphine) (96 mg, 0.083 mmol) in toluene/water (10:1, 10 ml) was stirred at 110° C. for 1.5 h under N2. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The mixture was washed with water and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by silica-gel column chromatography (3:1 to 1:3 hexane:ethyl acetate) to give the title compound (0.23 mg, 62%) as a pale yellow solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe resulting residue was purified by silica-gel column chromatography (3:1 to 1:3 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-680b95cf41e847639bb39e5c7d5d48e0
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487117B2

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