3-Hydroxypyridine → HCID 89783557, compound

HRID 1055869Notes

Reaction equation

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

Participants

Reactant 3

HCID 79713-Hydroxypyridine

HCID 24758Sodium hydride

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

Product 1

HCID 89783557HCID 89783557, compoundYield 27.3%

Conditions

Temperature: 25 °C

Procedure

Prepared according to Example 103, using NaH as a 60% dispersion in mineral oil (153 μl, 3.53 mmol, Sigma Aldrich), pyridin-3-ol (335 mg, 3.53 mmol, Sigma Aldrich), and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 150 mg, 0.504 mmol) and stirring at 25° C. for 6 h. Purification by column chromatography (silica gel, 0 to 9% MeOH/DCM) followed by trituration with MeOH provided 2-(2-(3-pyridinyloxy)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (49 mg, 27.3%). 1H NMR (400 MHz, CDCl3) δ ppm 11.07-11.15 (1H, m) 8.72-8.76 (2H, m) 8.68 (1H, d, J=1.00 Hz) 8.26 (1H, d, J=1.00 Hz) 8.04-8.09 (1H, m) 7.61-7.70 (2H, m) 7.45-7.57 (2H, m) 7.09-7.14 (1H, m) 5.38 (1H, br. s) 3.52-3.59 (2H, m) 2.54 (2H, t, J=1.00 Hz). m/z (ESI, +ve) 357.0 (M+H)+.

Workup

customPrepared
customPurification by column chromatography (silica gel, 0 to 9% MeOH/DCM)

Sources & evidence

ORD record: ord-bbf90ed1216a40679d207b787dd525a0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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