2-Chloro-6-methoxyquinoline → HCID 46931568, compound

HRID 2361477Notes

Reaction equation

HRID 2361477 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][CH:17]=1>>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:19]1[CH:20]=[CH:21][C:16]([NH:15][CH3:14])=[CH:17][CH:18]=1)[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 836472-Chloro-6-methoxyquinolineHCID 11957892N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 46931568HCID 46931568, compound

Procedure

4-(6-Methoxyquinolin-2-yl)-N-methylaniline T523 was prepared using general procedure A from 2-chloro-6-methoxyquinoline (39 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). T523 was obtained as a brown solid (27 mg, 51%). NMR (400 MHz, CDCl3): δ 8.03-7.99 (m, 4H), 7.75 (d, J=8.4 Hz, 1H), 7.33 (dd, J=9.2, 2.8 Hz, 1H), 7.04 (d, J=2.8 Hz, 1H), 6.71 (m, 2H), 3.92 (s, 3H), 2.89 (s, 3H); MS (ESI): 235 (M+H+).

Sources & evidence

ORD record
ord-7f45ee153a6f45ce994e1649516b115c
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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