6-Bromoquinoline → N,N-Dimethyl-4-(quinolin-6-yl)aniline

HRID 2361474Notes

Reaction equation

HRID 2361474 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH3:12][N:13]([CH3:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1>>[CH3:12][N:13]([CH3:23])[C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[CH:5]3)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 792436-BromoquinolineHCID 27343444-(Dimethylamino)phenylboronic acid

Product 1

HCID 58362492N,N-Dimethyl-4-(quinolin-6-yl)aniline

Procedure

N,N-Dimethyl-4-(quinolin-6-yl)aniline T505 was prepared using general procedure A from 6-bromoquinoline (52 mg, 0.25 mmol) and (4-(dimethylamino)phenyl)boronic acid (41 mg, 0.25 mmol). The product T505 was obtained as a yellow solid (42 mg, 67%). 1H NMR (400 MHz, CDCl3): δ 8.85 (dd, J=4.4, 1.6 Hz, 1H), 8.15 (m. 2H), 7.97 (dd, J=8.4, 1.6 Hz, 1H), 7.92 (d, J=2.0 Hz, 1H), 7.63 (m, 2H), 7.38 (dd, J=8.4, 4.4 Hz, 1H), 6.84 (m, 2H), 3.01 (s, 6H); MS (ESI): 249 (M+H+).

Sources & evidence

ORD record
ord-01d0668f435847df9de3ae93b6ad3475
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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