Methyl 5-chloropyrazine-2-carboxylate → 5-(6-Hydroxynaphthalen-2-yl)pyrazine-2-carboxylic acid

HRID 1771454Notes

Reaction equation

HRID 1771454 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](B(O)O)[CH:6]=[CH:5]2.Cl[C:16]1[N:17]=[CH:18][C:19]([C:22]([O:24]C)=[O:23])=[N:20][CH:21]=1>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:16]1[N:17]=[CH:18][C:19]([C:22]([OH:24])=[O:23])=[N:20][CH:21]=1)[CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 4349738(6-Hydroxynaphthalen-2-yl)boronic acid

Product 1

HCID 1360695075-(6-Hydroxynaphthalen-2-yl)pyrazine-2-carboxylic acid

Procedure

Followed the two step procedure described for Example 7 starting from 6-hydroxynaphthalen-2-ylboronic acid and methyl 5-chloropyrazine-2-carboxylate. 1H-NMR (MeOD-d4 500 MHz): 9.31 (s, 2H), 8.64 (s, 1H), 8.19-8.21 (d, J=9.0 Hz, 1H), 7.90-7.91 (d, J=8.5 Hz, 1H), 7.80-7.82 (d, J=8.5 Hz, 1H), 7.15-7.18 (t, J=2.0, 10.0 Hz, 2H). MS (ESI): m/z=267.0 [M+1]+.

Sources & evidence

ORD record
ord-06f62313145043f6a4790b492d2c24b7
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

Loading…