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Sodium Carbonate → N-[3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl]prop-2-enamide

HRID 1500824
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인쇄 미리보기

반응식

HRID 1500824 반응식
[C:1](NC1C=C(B(O)O)C=CC=1)(=O)C=C.C(=O)([O-])[O-].[Na+].[Na+].[CH3:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=3)[CH:29]=2)[NH:24]N=1>C(O)C.C(Cl)Cl>[CH3:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=3)[CH:29]=2)[NH:24][CH:1]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 103213313-Acrylamidophenylboronic acidHCID 178460022HCID 178460022, 화합물

생성물 1

HCID 86301143N-[3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl]prop-2-enamide

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane
용매
2회

반응 조건

온도
90 °C

실험 절차

A solution of 19 (50 mg, 0.2369 mmol) and 2 (50 mg, 0.2369 mmol) in ethanol and toluene (1:4 mL) was added sodium carbonate (49.74 mg, 0.4738 mmol). The reaction was degassed and purged with nitrogen for 15 min. Pd(dppf)Cl2.DCM (9.06 mg, 0.0114 mmol), and again degassed for 15 min. The reaction mixture was stirred for 2 h at 90° C. and the reaction mixture allowed to cool to rt and diluted with DCM (25 mL). The organic layer was filtered through Celite and concentrated to get the crude. The resulting oil was purified via silica gel chromatography using a gradient of 30% ethyl acetate:hexane to afford Compound 20. MS-ES+277 1H NMR (400 MHz, DMSO-D6) 20: 11.37 (d, 1H), 10.24 (d, 1H), 8.45 (d, 1H), 8.09 (d, 2H), 7.68 (d, 1H), 7.43 (d, 2H), 7.28 (d, 1H), 6.46 (d, 1H), 6.44 (d, 1H), 5.79 (d, 1H), 2.30 (d, 1H).

후처리

  1. customThe reaction was degassed
  2. custompurged with nitrogen for 15 min
  3. temperatureto cool to rt
  4. filtrationThe organic layer was filtered through Celite
  5. concentrationconcentrated
  6. customto get the crude
  7. customThe resulting oil was purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-f3d918c6ae28492aba217855d6b9c3a3
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206188B2

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