4-Bromopyridinium chloride → HCID 58930644, compound

HRID 1661512Notes

Reaction equation

HRID 1661512 reaction equation
Cl.BrC1C=CN=CC=1.N1C=CC([NH:15][C@H:16]2[CH2:20][CH2:19][N:18]([C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH2:17]2)=CC=1>>[NH2:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:21]2[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])=[CH:23][CH:22]=2)[CH2:17]1

Participants

3

Reactant 2

HCID 881004-Bromopyridinium chlorideHCID 58417037HCID 58417037, compound

Product 1

HCID 58930644HCID 58930644, compoundYield 77%

Procedure

Staring from 4-bromopyridine hydrochloride (16) (356 mg, 1.83 mmol) and compound 17 (400 mg, 1.52 mmol) title compound 18 was obtained (398 mg, 77% yield) according to the known procedure (Harris, M. C.; Geis, O.; Buchwald, S. L.*; J. Org. Chem., 1999, 64, 6019-6022). 1H NMR: (DMSO-d6) δ(ppm): 8.58 (d, J=6.5 Hz, 1H), 8.18 (d, J=6.5 Hz, 2H), 7.72 (d, J=8.8 Hz, 2H), 6.91 (d, J=6.8 Hz, 2H), 6.58 (d, J=9.0 Hz, 2H), 4.46-4.40 (m, 1H), 3.71 (dd, J=10.6, 6.3 Hz, 1H), 3.48 (dt, J=9.6, 7.6 Hz, 1H), 4.42 (td, J=9.8, 4.9 Hz, 1H), 3.27 (dd, J=10.4, 3.3 Hz, 1H), 2.35 (sext, J=7.2 Hz, 1H), 2.05-1.98 (m, 1H), 1.50 (s, 9H). LRMS (ESI): (calc) 339.19 (found) 340.2 (MH+).

Sources & evidence

ORD record
ord-0cf0260ad0ba44369c089ffbfcc0372f
Source dataset
uspto-grants-2011_10
Patent number
US08030344B2

Reaction notes

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