Potassium Acetate → HCID 89784303, compound

HRID 1055934Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:22]1([C:28](B(O)O)=[CH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC([O-])=O.[K+]>CCO>[C:22]1([C:28]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([C:12]4[NH:20][C:19]5[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=5[CH:13]=4)[CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 200 mg, 0.672 mmol), (1-phenylvinyl)boronic acid (Aldrich; 139.1 mg, 0.941 mmol), PdCl2(APhos)2 (23.8 mg, 0.034 mmol), and KOAc (131.8 mg, 1.34 mmol) in EtOH (3.4 mL) was stirred under argon in a sealed tube at 80° C. for 23 h. The mixture was concentrated onto silica gel, and chromatographically purified (silica gel, 0-10% MeOH/DCM) to provide 2-(2-(1-phenylvinyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (189.2 mg, 0.518 mmol, 77% yield) as an orange solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.05 (1H, br. s.), 8.23 (1H, d, J=8.8 Hz), 8.08 (1H, d, J=7.4 Hz), 7.81 (1H, d, J=8.6 Hz), 7.64 (1H, d, J=8.0 Hz), 7.54 (1H, d, J=7.8 Hz), 7.46-7.52 (2H, m), 7.41-7.46 (3H, m), 7.14 (1H, s), 6.01 (1H, s), 5.85 (1H, s), 5.47 (1H, br. s.), 3.47 (2H, td, J=6.9, 1.9 Hz), 2.33 (2H, t, J=6.8 Hz). m/z (ESI, +ve) 366.2 (M+H)+.

Workup

concentrationThe mixture was concentrated onto silica gel
customchromatographically purified (silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record: ord-1918f28041e74b9e981ebe18fb5edc17
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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