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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
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HRID 630549 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

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)

후처리

  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]

출처 및 근거

ORD 기록
ord-ae184684a3454d3cb839a24f4e366ad9
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315490B2

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