2,6-Dimethylphenol → HCID 89793618, compound

HRID 1055924Notes

Reaction equation

HRID 1055924 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].Cl[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([C:21]3[NH:29][C:28]4[CH2:27][CH2:26][NH:25][C:24](=[O:30])[C:23]=4[CH:22]=3)[CH:15]=[CH:16][CH:17]=2)[N:12]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([C:21]3[NH:29][C:28]4[CH2:27][CH2:26][NH:25][C:24](=[O:30])[C:23]=4[CH:22]=3)[CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

3

Reactant 2

HCID 113352,6-DimethylphenolHCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89793618HCID 89793618, compoundYield 80%

Conditions

Temperature
70 °C

Procedure

Prepared according to Example 103 using 2,6-dimethylphenol (158 mg, 1.293 mmol) and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50.0 mg, 0.168 mmol), heating at 70° C. for 17 h. Chromatographic purification (silica gel, 0-10% MeOH/DCM) furnished 2-(2-(2,6-dimethylphenoxy)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (51.4 mg, 0.134 mmol, 80% yield) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ ppm 11.08 (1H, br. s.), 8.21 (1H, d, J=8.8 Hz), 8.03 (1H, dd, J=7.6, 1.3 Hz), 7.61 (1H, dd, J=7.9, 1.3 Hz), 7.42 (1H, t, J=7.8 Hz), 7.29 (1H, s), 7.21 (3H, s), 7.10 (1H, d, J=2.2 Hz), 5.33 (1H, br. s.), 3.51 (2H, td, J=6.8, 1.2 Hz), 2.47 (2H, t, J=6.9 Hz), 2.17 (6H, s). m/z (ESI, +ve) 384.2 (M+H)+.

Workup

  1. customPrepared
  2. customChromatographic purification (silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-6b34999e6d6b45a29fed95b577207b9a
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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