3-Pyridinylboronic acid → HCID 24852686, compound

HRID 659333Notes

Reaction equation

HRID 659333 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16](I)=[CH:17][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21](B(O)O)[CH:20]=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:21]3[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=3)=[CH:17][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 578858821,2,3,4-Tetrahydro-7-iodo-1-(phenylmethyl)pyrido[2,3-b]pyrazine

Product 1

HCID 24852686HCID 24852686, compoundYield 23%

Procedure

1-Benzyl-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (30 mg) was reacted with pyridine 3-boronic acid as in General Procedure 4A to give the title compound as a light yellow film (23% yield). M.p. (film), LCMS: m/z=303.40 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.41-3.44 m, 2H), 3.60-3.63 (m, 2H), 4.49 (s, 2H), 6.80 (s, 1H), 5.40 (bs, 1H), 6.80 (s, 1H), 7.27-7.42 (m, 5H), 7.64 (s, 1H), 7.65 (d, J=7.8 Hz, 1H), 8.48 (d, J=4.8 Hz, 1H), 8.63 (s, 1H).

Sources & evidence

ORD record
ord-cba0e0f4a6a44a4393ebafb8ff96c922
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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