4-Fluorobenzyl bromide → Methyl 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

HRID 714298Notes

Reaction equation

HRID 714298 reaction equation
Br[CH2:2]C1C=CC(F)=CC=1.Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1.[O:20]=[C:21]1[NH:25][CH2:24][CH2:23][N:22]1[C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][N:34]=1)[C:29]([O-:31])=[O:30]>>[F:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[F:18])[CH2:11][N:25]1[CH2:24][CH2:23][N:22]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][N:34]=2)[C:29]([O:31][CH3:2])=[O:30])[C:21]1=[O:20]

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 866530512-(2-Oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 58247785Methyl 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinateYield 66%

Procedure

Following the procedure as described in Preparation 17, making variations as required to replace 1-(bromomethyl)-4-fluorobenzene with 4-(bromomethyl)-1,2-difluorobenzene to react with 2-(2-oxoimidazolidin-1-yl)isonicotinate, methyl 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate was obtained as a colorless solid in 66% yield: 1H NMR (300 MHz, CDCl3) δ 8.86-8.85 (m, 1H), 8.37 (dd, J=5.1, 0.6 Hz, 1H), 7.47-7.45 (m, 1H), 7.16-7.01 (m, 3H), 4.43 (s, 2H), 4.05 (t, J=8.0 Hz, 2H), 3.92 (s, 3H), 3.38 (t, J=8.0 Hz, 2H); MS (ES+) m/z 348.0 (M+1).

Workup

  1. customas described in Preparation 17

Sources & evidence

ORD record
ord-25bcc6b5d97a4607b7711bac90b0482b
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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