3-Chlorophenol → HCID 89783719, compound

HRID 1055871Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Cl[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[C:15]([C:22]3[NH:30][C:29]4[CH2:28][CH2:27][NH:26][C:25](=[O:31])[C:24]=4[CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[N:13]=1>>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[C:15]([C:22]3[NH:30][C:29]4[CH2:28][CH2:27][NH:26][C:25](=[O:31])[C:24]=4[CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

Reactant 3

HCID 79333-Chlorophenol

HCID 24758Sodium hydride

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

Product 1

HCID 89783719HCID 89783719, compoundYield 19.1%

Conditions

Temperature: 85 °C

Procedure

Prepared according to Example 103, NaH as a 60% dispersion in mineral oil (143 μl, 3.29 mmol, Sigma Aldrich), 3-chlorophenol (334 μl, 3.29 mmol, Sigma Aldrich), and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 140 mg, 0.470 mmol) and stirring at 85° C. for 17 h. Purification by column chromatography (silica gel, 0 to 60% EtOAc/DCM then 5% MeOH/DCM) providing 2-(2-(3-chlorophenoxy)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (35 mg, 19%). 1H NMR (400 MHz, CDCl3) δ ppm 11.28-11.38 (1H, m) 8.23 (1H, d, J=1.00 Hz) 8.04-8.09 (1H, m) 7.61-7.66 (1H, m) 7.48 (2H, q, J=1.00 Hz) 7.36-7.41 (2H, m) 7.19-7.26 (3H, m) 5.84-6.01 (1H, m) 3.58 (2H, t, J=1.00 Hz) 2.55 (2H, t, J=1.00 Hz). m/z (ESI, +ve) 390.0 (M+H)+.

Workup

customPrepared
customPurification by column chromatography (silica gel, 0 to 60% EtOAc/DCM

Sources & evidence

ORD record: ord-61211556ede94060a43a390e556edf68
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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