1-(2,5-Dichlorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazine → 1-(2,5-Dichlorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carbonitrile

HRID 659397Notes

Reaction equation

HRID 659397 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13](I)=[CH:14][C:6]1=2.[C:21]([Cu])#[N:22]>>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:21]#[N:22])=[CH:14][C:6]1=2

Participants

3

Reactant 2

HCID 578860791-(2,5-Dichlorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazineHCID 178418546HCID 178418546, compound

Product 1

HCID 578861111-(2,5-Dichlorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carbonitrileYield 46%

Procedure

1-(2,5-Dichlorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (2.0 g) was reacted with CuCN as in General Procedure 6 to give the title compound as an off-white solid (46% yield). M.p. 221-222° C., LCMS: m/z=320.77 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 3.28 (t, J=4.6 Hz, 2H), 3.45-3.54 (m, 2H), 4.48 (s, 2H), 6.69 (s, 1H), 7.29 (d, J=2.5 Hz, 1H), 7.41 (dd, J=8.6 Hz, 2.5 Hz, 1H), 7.54 (d, J=8.6 Hz, 1H), 7.67 (bs, 1H), 7.75 (d, J=1.8 Hz, 1H).

Sources & evidence

ORD record
ord-a7eef2cd8ae142d4aa2b77868cd42f11
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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