Sodium Carbonate → HCID 89784607, compound

HRID 1056314Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8](Cl)=[N:7]2.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:7]2

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 8-bromo-N-(tert-butyl)-3-chloroquinoxalin-2-amine (Example 304a (˜2.5:1 mixture with 5-bromo-N-(tert-butyl)-3-chloroquinoxalin-2-amine); 119.0 mg, 0.378 mmol), phenylboronic acid (Aldrich; 46.1 mg, 0.378 mmol), Na2CO3 (200 mg, 1.891 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 21.85 mg, 0.019 mmol) in a mixture of MeCN (3.0 mL) and water (1.000 mL) was stirred under argon at 80° C. for 17.5 h. The reaction mixture was cooled to RT and concentrated onto silica gel. Chromatographic purification (silica gel, 0-10% EtOAc/hexanes) furnished 8-bromo-N-(tert-butyl)-3-phenylquinoxalin-2-amine (83.0 mg, 0.233 mmol, 62% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.85 (1H, dd, J=4.5, 1.2 Hz), 7.83 (1H, dd, J=5.1, 1.4 Hz), 7.67-7.72 (2H, m), 7.51-7.59 (3H, m), 7.20 (1H, t, J=7.8 Hz), 5.23 (1H, br. s.), 1.57 (9H, s). m/z (ESI, +ve) 355.9/358.0 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to RT
concentrationconcentrated onto silica gel
customChromatographic purification (silica gel, 0-10% EtOAc/hexanes)

Sources & evidence

ORD record: ord-68fa6edc32964221a0330ca324c1799b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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