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Potassium Carbonate → (1-(5-(4-Cyclopropylpyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

HRID 630549
ノート
印刷プレビュー

反応式

HRID 630549 の反応式
B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:25]1[CH:26]=[N:27][C:28]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([C:40]([N:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[O:41])[CH:38]=3)[C:33]([S:47][CH3:48])=[CH:32]2)=[N:29][CH:30]=1.Br[C:50]1[CH:55]=[C:54]([CH:56]2[CH2:58][CH2:57]2)[CH:53]=[CH:52][N:51]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:56]1([C:54]2[CH:53]=[CH:52][N:51]=[C:50]([C:25]3[CH:30]=[N:29][C:28]([N:31]4[C:39]5[C:34](=[CH:35][CH:36]=[C:37]([C:40]([N:42]6[CH2:43][CH2:44][CH2:45][CH2:46]6)=[O:41])[CH:38]=5)[C:33]([S:47][CH3:48])=[CH:32]4)=[N:27][CH:26]=3)[CH:55]=2)[CH2:58][CH2:57]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 457879032-Bromo-4-cyclopropylpyridineHCID 118676809(1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

生成物 1

HCID 118676890
(1-(5-(4-Cyclopropylpyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

試薬・触媒・溶媒 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

Bis(pinacolato)diboron (0.584 g, 2.3 mmol) and potassium acetate (0.421 g, 4.29 mmol) were added at room temperature to a solution of 341a) (0.6 g, 1.43 mmol) in dry dioxane (35 mL). The reaction apparatus was flushed with argon, PdCl2(dppf) (58 mg, 0.071 mmol) was added and the resulting mixture was stirred for 1 h at 110° C. (complete consumption of starting material). 2-bromo-4-cyclopropyl-pyridine (0.328 g, 2.14 mmol), potassium carbonate (2M, 2.5 mL) and tetrakis(triphenylphosphine)palladium(0) (83 mg, 0.071 mmol) were added successively and the reaction mixture was stirred for 16 h at 100° C. The mixture was then cooled to ambient temperature and filtered through a sintered funnel. The filtrate was concentrated and the remnant was purified by flash column chromatography [silica; dichloromethane with 2% methanol]. White solid. Yield: 0.28 g (43% of theory)

後処理

  1. additionwas added
  2. custom(complete consumption of starting material)
  3. stirringthe reaction mixture was stirred for 16 h at 100° C
  4. temperatureThe mixture was then cooled to ambient temperature
  5. filtrationfiltered through a sintered funnel
  6. concentrationThe filtrate was concentrated
  7. customthe remnant was purified by flash column chromatography [silica; dichloromethane with 2% methanol]

出典と根拠

ORDレコード
ord-ae184684a3454d3cb839a24f4e366ad9
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315490B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート