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Cesium carbonate → tert-butyl 4-(4-(2-(methylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 522230
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HRID 522230 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12.[CH3:24][NH:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=[CH:28][N:27]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH3:24][NH:25][C:26]1[C:31]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][C:9]([C:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=4)=[CH:10][C:3]=23)=[CH:30][CH:29]=[CH:28][N:27]=1
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참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 72218845N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2-amineHCID 118274390tert-butyl 4-(4-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 118274083tert-butyl 4-(4-(2-(methylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of Example 135D (170 mg, 0.45 mmol), N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (105 mg, 0.45 mmol), bis(triphenylphosphine)palladium(II) chloride (31 mg, 0.045 mmol), tricyclohexylphosphine (13 mg, 0.045 mmol) and cesium carbonate (443 mg, 1.34 mmol) in a round bottom flask was purged with nitrogen. Dioxane (10 mL) was added and the mixture was heated at 100° C. overnight. After cooling, the mixture was triturated with dichloromethane (200 mL) and filtered. The filtrate was concentrated and the residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane) to provide the title compound. MS (ESI+) m/z 406 (M+1).

후처리

  1. temperatureAfter cooling
  2. customthe mixture was triturated with dichloromethane (200 mL)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-ffaee0bba07147e3aa9536e63fd3dd65
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09328112B2

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