2-(Bromomethyl)-4-chloro-1-(trifluoromethyl)benzene → HCID 57886085, compound

HRID 2074608Notes

Reaction equation

HRID 2074608 reaction equation
[I:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][C:8](=O)[NH:9][C:4]=2[CH:3]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:22]([F:25])([F:24])[F:23])=[C:18]([CH:21]=1)[CH2:19]Br.ClC1C=CC(C(F)(F)F)=CC=1CN1C(=O)CNC2N=CC(I)=CC1=2>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:22]([F:23])([F:24])[F:25])=[C:18]([CH:21]=1)[CH2:19][N:9]1[CH2:8][CH2:7][NH:6][C:5]2[N:11]=[CH:12][C:2]([I:1])=[CH:3][C:4]1=2

Participants

4

Reactant 3

HCID 27781162-(Bromomethyl)-4-chloro-1-(trifluoromethyl)benzeneHCID 448291147-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-oneHCID 57886049HCID 57886049, compound

Product 1

HCID 57886085HCID 57886085, compoundYield 17%

Procedure

7-Iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (968 mg) was reacted with 5-chloro-2-(trifluoromethyl)benzyl bromide as in General Procedure 1. The resulting 1-(2-chloro-5-trifluoromethylbenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one was reduced as in General Procedure 2 to give the title compound as an orange solid (17% yield). M.p. 189-191° C., LCMS: m/z=454.08 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 3.28-3.34 (m, 2H), 3.41-3.46 (m, 2H), 4.53 (s, 2H), 6.52 (s, 1H), 6.75 (s, 1H), 7.44 (s, 2H), 7.59 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H).

Sources & evidence

ORD record
ord-cf2894e8f8784d75a5d9a3eb13b48c66
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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