1-Methyl-1H-indole-5-boronic acid → ethyl 2-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylate

HRID 1930387ノート

反応式

HRID 1930387 の反応式
C([O-])(O)=O.[Na+].C1(C)C=CC=CC=1.C(O)C.Cl[C:17]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=[C:19]([CH3:28])[N:18]=1.[CH3:29][N:30]1[C:38]2[C:33](=[CH:34][C:35](B(O)O)=[CH:36][CH:37]=2)[CH:32]=[CH:31]1>C(OCC)(=O)C.O.[Pd].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>[CH3:28][C:19]1[N:18]=[C:17]([C:35]2[CH:34]=[C:33]3[C:38](=[CH:37][CH:36]=2)[N:30]([CH3:29])[CH:31]=[CH:32]3)[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=1

参加物

7

反応物 3

HCID 27598671-Methyl-1H-indole-5-boronic acidHCID 12677176Ethyl 4-chloro-2-methylpyrimidine-5-carboxylateHCID 86620166NaHCO3 toluene ethanol

生成物 1

HCID 69037048ethyl 2-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylate収率 53%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

In a mixture of saturated NaHCO3:toluene:ethanol (1:2:1) (12 mL) was dissolved ethyl 4-chloro-2-methylpyrimidine-5-carboxylate (500 mg, 2.49 mmol), N-methylindole-5-boronic acid (872 mg, 4.98 mmol) and to this was added tetrakis(triphenylphosphine)-palladium(0) (58 mg). The reaction stirred at 75° C., under Ar, overnight. The reaction was allowed to cooled to RT, diluted with ethyl acetate (25 mL) and water (25 mL) and filtered free of insolubles. The organic phase was washed with 5% citric acid (25 mL), saturated sodium bicarbonate (25 mL) and brine (25 mL), evaporated at reduced pressure to give a reddish thick foam, and purified by chromatography (Biotage Si-25 column, 15-40% ethyl acetate/hexane) to give ethyl 2-methyl-4-(1-methyl-1 H-indol-5-yl)pyrimidine-5-carboxylate as a thick clear oil. The oil solidified overnight (391 mg, 53% yield). MS (ESI) m/z: 296.0 (M+H+).

後処理

  1. temperatureto cooled to RT
  2. filtrationfiltered free of insolubles
  3. washThe organic phase was washed with 5% citric acid (25 mL), saturated sodium bicarbonate (25 mL) and brine (25 mL)
  4. customevaporated at reduced pressure
  5. customto give a reddish thick foam
  6. custompurified by chromatography (Biotage Si-25 column, 15-40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-109fc1e01d8542ecb36f81c627129614
出典データセット
uspto-grants-2012_05
特許番号
US08188113B2

反応ノート

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