6-Bromoquinoline → N-Methyl-4-(quinolin-6-yl)aniline

HRID 2361475Notes

Reaction equation

HRID 2361475 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][NH:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=1>>[CH3:12][NH:13][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 11957892N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 59489478N-Methyl-4-(quinolin-6-yl)aniline

Procedure

N-Methyl-4-(quinolin-6-yl)aniline T514 was prepared using general procedure A from 6-bromoquinoline (41 mg, 0.2 mmol) and N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (46 mg, 0.2 mmol). The product T514 was obtained as a black solid (20 mg, 43%). 1H NMR (400 MHz, CDCl3): δ 8.86 (dd, J=4.4, 1.6 Hz, 1H), 8.18 9m, 1H), 8.13 (d, J=9.2 Hz, 1H), 7.96 (dd, J=8.8, 2.4 Hz, 1H), 7.92 (d, J=2.0 Hz, 1H), 7.59 (m, 2H), 7.40 (dd, J=8.4, 4.4 Hz, 1H), 6.74 (m, 2H), 2.91 (s, 3H); MS (ESI): 235 (M+H+).

Sources & evidence

ORD record
ord-d3c7e98554c34defab44fe3fc81e1641
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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