2-Chloroquinoline → 2-(1H-Indol-5-yl)quinoline

HRID 452313Notes

Reaction equation

HRID 452313 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.C[N:13]1[C:21]2[C:16](=[CH:17][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1>>[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

3

Reactant 2

HCID 119282-ChloroquinolineHCID 162177781-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 583623512-(1H-Indol-5-yl)quinoline

Procedure

2-(1H-indol-5-yl)quinoline was prepared using general procedure A from 2-chloroquinoline (32 mg, 0.2 mmol) and 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (51 mg, 0.2 mmol). The product was obtained as off-white solid (22 mg, 42%). MS (ESI): 245 (M+H+).

Sources & evidence

ORD record
ord-b334fb72d10c47d990f76a3c0e65da3d
Source dataset
uspto-grants-2013_07
Patent number
US08491869B2

Reaction notes

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