Potassium Phosphate, Tribasic → 2-(2-methyl-3-phenylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056305노트

반응식

HRID 1056305 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([CH3:12])=[N:7]2.CC1(C)C(C)(C)OB([C:27]2[NH:35][C:34]3[CH2:33][CH2:32][NH:31][C:30](=[O:36])[C:29]=3[CH:28]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.C(Cl)Cl>[CH3:12][C:6]1[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:27]2[NH:35][C:34]3[CH2:33][CH2:32][NH:31][C:30](=[O:36])[C:29]=3[CH:28]=2)[N:7]=1

참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 897821025-Bromo-2-methyl-3-phenylquinoxalineHCID 897834962-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-C]pyridin-4-one

생성물 1

HCID 897852802-(2-methyl-3-phenylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one수율 32%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매HCID 21226129Dichloromethane methanol용매

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온도
100 °C

실험 절차

A solution of 5-bromo-2-methyl-3-phenylquinoxaline (87.5 mg, 0.292 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 609; 216 mg, 0.585 mmol), K3PO4 (186 mg, 0.877 mmol), XPhos (Strem Chemicals, Inc.; 13.94 mg, 0.029 mmol), and Pd2dba3 (Aldrich; 13.39 mg, 0.015 mmol) in a mixture of 1,4-dioxane (2.0 mL) and water (0.400 mL) was stirred under argon at 100° C. for 45 min. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) to provide 2-(2-methyl-3-phenylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (32.8 mg, 0.093 mmol, 32% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.81 (1H, br. s.), 8.06 (1H, dd, J=7.2, 1.4 Hz), 7.77-7.91 (4H, m), 7.53-7.64 (3H, m), 7.26 (1H, d, J=2.2 Hz), 7.00 (1H, s), 3.40 (2H, td, J=6.8, 2.4 Hz), 2.84 (2H, t, J=6.8 Hz), 2.75 (3H, s). m/z (ESI, +ve) 355.0 (M+H)+.

후처리

  1. concentrationThe reaction mixture was then concentrated onto silica gel
  2. customchromatographically purified (silica gel, 0-100% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-534f14bf23ee47ae8f0ba4a6758dc55c
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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