4-Fluorobenzyl bromide → Methyl 2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinate
Reaction equation
Br[CH2:2]C1C=CC(F)=CC=1.Br.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[O:19]=[C:20]1[NH:24][CH2:23][CH2:22][N:21]1[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][N:33]=1)[C:28]([O-:30])=[O:29]>>[O:19]=[C:20]1[N:24]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:23][CH2:22][N:21]1[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][N:33]=1)[C:28]([O:30][CH3:2])=[O:29]Participants
Procedure
Following the procedure as described in Preparation 17, making variations as required to replace 1-(bromomethyl)-4-fluorobenzene with 2-(bromomethyl)pyridine hydrobromide to react with 2-(2-oxoimidazolidin-1-yl)isonicotinate, methyl 2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinate was obtained as a colorless solid in 66% yield: mp 100-102° C.; 1H NMR (300 MHz, CDCl3) δ 8.88 (d, J=0.9 Hz, 1H), 8.55 (d, J=4.8 Hz, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.70-7.64 (m, 1H), 7.46-7.44 (m, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.22-7.18 (m, 1H), 4.62 (s, 2H), 4.07 (t, J=8.1 Hz, 2H), 3.90 (s, 3H), 3.54 (t, J=8.1 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.9, 157.0, 156.6, 153.4, 149.3, 148.0, 138.7, 137.2, 122.7, 122.4, 116.7, 112.5, 52.6, 49.6, 41.9, 41.5; MS (ES+) m/z 312.9 (M+1).
Workup
- customas described in Preparation 17
Sources & evidence
- ORD record
- ord-4510e53ee11640abaead97c755a5fd81
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187426B2
Reaction notes
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