2-Chloroquinoline → HCID 46931464, compound

HRID 2361462Notes

Reaction equation

HRID 2361462 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[N:24][CH:25]=2)O1>>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:20]1[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[N:24][CH:25]=1

Participants

3

Reactant 2

HCID 119282-ChloroquinolineHCID 164141882-Cyanopyridine-5-boronic acid pinacol ester

Product 1

HCID 46931464HCID 46931464, compoundYield 3%

Procedure

A from 2-chloroquinoline (82 mg, 0.5 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (115 mg, 0.5 mmol). The product was obtained as yellow solid (3 mg, 3%). 1H NMR (400 MHz, CDCl3): δ 9.48 (dd, J=2.4, 0.8 Hz, 1H), 8.69 (dd, J=8.0, 2.0 Hz, 1H), 8.33 (d, J=8.8 Hz, 1H), 8.19 (d, J=8.4 Hz, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.90 (dd, J=8.4, 1.2 Hz, 1H), 7.87 (dd, J=8.4, 0.8 Hz, 1H), 7.81 (m, 1H), 7.63 (m, 1H); MS (ESI):232 (M+H+).

Sources & evidence

ORD record
ord-eadb184dba674456abde89875fa14bf6
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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