Sodium Carbonate → HCID 89782102, 화합물

HRID 1056304

반응식

HRID 1056304 반응식
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5](Cl)[C:6]([CH3:12])=[N:7]2.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N.O.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>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([CH3:12])=[N:7]2

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 894288875-Bromo-3-chloro-2-methylquinoxaline

생성물 1

HCID 89782102HCID 89782102, 화합물수율 89.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

A suspension of 5-bromo-3-chloro-2-methylquinoxaline (126e; 327 mg, 1.270 mmol), phenylboronic acid (Aldrich; 155 mg, 1.270 mmol), Na2CO3 (673 mg, 6.35 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 73.4 mg, 0.063 mmol) in a mixture of CH3CN (9.00 mL) and water (3 mL) was stirred under argon at 80° C. for 16 h. The reaction was cooled to RT and concentrated onto silica gel. Chromatographic purification (silica gel, 0-40% EtOAc/hexanes) furnished 5-bromo-2-methyl-3-phenylquinoxaline (340.0 mg, 1.136 mmol, 89% yield) as a peach-colored solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.03 (2H, d, J=7.8 Hz), 7.77 (2H, dd, J=7.9, 1.7 Hz), 7.60 (1H, d, J=7.8 Hz), 7.48-7.57 (3H, m), 2.85 (3H, s). m/z (ESI, +ve) 298.9/300.8 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to RT
  2. concentrationconcentrated onto silica gel
  3. customChromatographic purification (silica gel, 0-40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-97a9b42f9a714b5b81b92db715de0be9
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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