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

HRID 1930387노트

반응식

HRID 1930387 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-109fc1e01d8542ecb36f81c627129614
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188113B2

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