4-Fluorobenzyl bromide → HCID 58247794, compound

HRID 714299Notes

Reaction equation

HRID 714299 reaction equation
Br[CH2:2]C1C=CC(F)=CC=1.Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[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:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[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 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 866530512-(2-Oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 58247794HCID 58247794, compoundYield 64%

Procedure

Following the procedure as described in Preparation 17, making variations as required to replace 1-(bromomethyl)-4-fluorobenzene with 1-(bromomethyl)-2,4-difluorobenzene to react with 2-(2-oxoimidazolidin-1-yl)isonicotinate, methyl 2-(3-(2,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate was obtained as a colorless solid in 64% yield: 1H NMR (300 MHz, CDCl3) δ 8.85 (s, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.46-7.31 (m, 2H), 6.89-6.79 (m, 2H), 4.51 (s, 2H), 4.04 (t, J=8.1 Hz, 2H), 3.92 (s, 3H), 3.44 (t, J=8.1 Hz, 2H); MS (ES+) m/z 347.9 (M+1).

Workup

  1. customas described in Preparation 17

Sources & evidence

ORD record
ord-61cfb5e4d8d54a91aaaa868a4ce0c329
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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