2-Chloropyridine-4-boronic acid → HCID 57885920, compound

HRID 659418Notes

Reaction equation

HRID 659418 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[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.[Cl:21][C:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][N:23]=1>>[Cl:21][C:22]1[CH:27]=[C:26]([C:13]2[CH:12]=[N:11][C:7]3[NH:8][CH2:9][CH2:10][N:5]([CH2:4][C:3]4[C:2]([Cl:1])=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:20])[C:6]=3[CH:14]=2)[CH:25]=[CH:24][N:23]=1

Participants

3

Reactant 2

HCID 51515952-Chloropyridine-4-boronic acidHCID 57885814HCID 57885814, compound

Product 1

HCID 57885920HCID 57885920, compoundYield 31%

Procedure

1-(2,6-Dichlorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (511 mg) was reacted with 2-chloropyridine-4-boronic acid as in General Procedure 4B to give the title compound as a yellow solid (31% yield). M.p.=194° C., LCMS: m/z=405.56 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.17 (2H, t, J=4.8 Hz), 3.53 (2H, m), 4.62 (2H, s), 5.12 (1H, bs), 7.06 (1H, s), 7.42 (4H, m), 7.68 (1H, m), 7.81 (1H, d, J=1.8 Hz), 8.35 (1H, d, J=5.1 Hz).

Sources & evidence

ORD record
ord-a9e76f04e1e343d88138d2fc41b3a481
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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