Sodium Carbonate → methyl 5-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate

HRID 451366ノート

反応式

HRID 451366 の反応式
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]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1B(O)O.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]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH3:11]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 177502292-Chloro-4-fluorobenzeneboronic acidHCID 66924763Methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate

生成物 1

HCID 58488518methyl 5-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate収率 84.6%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 22272177Toluene water溶媒

反応条件

温度
110 °C

実験手順

A mixture of methyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (0.63 g, 2.8 mmol), (2-chloro-4-fluorophenyl)boronic acid (1.0 g, 5.7 mmol), Na2CO3 (0.91 g, 8.6 mmol) and palladium tetrakis(triphenylphosphine) (0.17 g, 0.14 mmol) in toluene/water (10:1, 25 ml) was stirred at 110° C. for 9.0 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 (6:1 to 1:1 hexane:ethyl acetate) to give the title compound (634 mg, 84%) as a white solid.

後処理

  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 (6:1 to 1:1 hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-89a792b4cf984429928c46ec9715c495
出典データセット
uspto-grants-2013_07
特許番号
US08487117B2

反応ノート

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