2-Chloro-5-iodopyridine → 9-Methyl-3-(6-chloro-3-pyridinyl)-3,9-diazabicyclo[4.2.1]nonane

HRID 914755Notes

Reaction equation

HRID 914755 reaction equation
[CH3:1][N:2]1[CH:8]2[CH2:9][CH2:10][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7]2.[Cl:11][C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][N:13]=1>>[CH3:1][N:2]1[CH:8]2[CH2:9][CH2:10][CH:3]1[CH2:4][N:5]([C:15]1[CH:14]=[N:13][C:12]([Cl:11])=[CH:17][CH:16]=1)[CH2:6][CH2:7]2

Participants

3

Reactant 2

HCID 43971762-Chloro-5-iodopyridineHCID 139737309-Methyl-3,9-diazabicyclo[4.2.1]nonane

Product 1

HCID 185451759-Methyl-3-(6-chloro-3-pyridinyl)-3,9-diazabicyclo[4.2.1]nonaneYield 78%

Procedure

9-Methyl-3,9-diazabicyclo[4.2.1]nonane (prepared as described in U.S. Pat. No. 2,999,091) and 2-chloro-5-iodopyridine were coupled according the procedure of Example 15C to provide the title compound (78% yield). 1H NMR (free base, CDCl3, 300 MHz) δ 1.23-1.48 (m, 2H), 1.65-1.76 (m, 1H), 1.91-2.27 (m, 3H), 2.44 (s, 3H), 3.18-3.35 (m, 3H), 3.48-3.54 (m, 2H), 3.65 (br d, J=13.5 Hz, 1H), 6.98 (dd, J=3, 8.25 Hz, 1H), 7.06 (d, J=8.25 Hz, 1H), 7.87 (d, J=3 Hz, 1H); MS (DCI/NH3) m/z 252 (M+H)+, 269 (M+NH4)+; Anal. Calcd. for C13H18ClN3.C7H8O3S: C, 56.66; H, 6.18; N, 9.91. Found: C, 56.76; H, 6.15; N, 9.77.

Sources & evidence

ORD record
ord-1fc14019dad248109c3ca2d52e6350be
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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