3-Aminopyridine → 8-bromo-N-(pyridin-3-yl)quinolin-2-amine

HRID 1055980Notes

Reaction equation

HRID 1055980 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=C[CH:14]=1)[CH:8]=[CH:7]2.BrC1C=CC=C2C=1[N:28]=C(Cl)C=C2.N1C=CC=C(N)C=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]1[CH:14]=[N:28][CH:16]=[CH:17][CH:18]=1)[CH:8]=[CH:7]2

Participants

5

Reactant 4

HCID 100093-AminopyridineHCID 2733832Lithium HexamethyldisilazideHCID 109557558-Bromo-2-chloroquinolineHCID 897821908-bromo-N-phenylquinolin-2-amine

Product 1

HCID 897818908-bromo-N-(pyridin-3-yl)quinolin-2-amineYield 57%

Procedure

This compound (1.03 g, 57% yield) as a tan crystalline solid was prepared similarly to that described in the preparation of 165c, using 8-bromo-2-chloroquinoline (Biofine International, Vancouver, BC; 1.46 g, 6.02 mmol), pyridin-3-amine (Aldrich; 0.68 g, 7.22 mmol), and LiHMDS (1.0 M solution in THF; 15.05 mL, 15.05 mmol) as starting materials. 1H NMR (400 MHz, DMSO-D6) δ ppm 9.93 (1H, s), 9.20 (1H, d, J=2.3 Hz), 8.84 (1H, d, J=8.4 Hz), 8.24-8.13 (2H, m), 7.99 (1H, d, J=7.6 Hz), 7.82 (1H, d, J=7.6 Hz), 7.39 (1H, dd, J=8.4, 4.7 Hz), 7.26 (1H, t, J=7.7 Hz), 7.18 (1H, d, J=8.8 Hz). m/z (ESI, +ve) 300/302 (M+H)+.

Sources & evidence

ORD record
ord-0de924f4e0924cb3bae886f9fee3270d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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