Sodium Carbonate → methyl 5-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylate

HRID 451362노트

반응식

HRID 451362 반응식
Br[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH3:11].[Cl: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]>[Cl: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 27632444-Chloro-2-(trifluoromethyl)phenylboronic AcidHCID 66924763Methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate

생성물 1

HCID 58488514methyl 5-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylate수율 65%

시약·촉매·용매 3

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

반응 조건

온도
110 °C

실험 절차

A mixture of methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (0.44 g, 2.0 mmol), [4-chloro-2-(trifluoromethyl)phenyl]boronic acid (0.90 g, 4.0 mmol), Na2CO3 (0.64 g, 6.0 mmol) and palladium tetrakis(triphenylphosphine) (0.12 g, 0.10 mmol) in toluene/water (9:1, 10 ml) was stirred at 110° C. for 2.0 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 (dichloromethane) to give the title compound (0.41 g, 65%) 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 (dichloromethane)

출처 및 근거

ORD 기록
ord-72fefe348b6a43c5bc1fcddcf9400c17
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487117B2

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