4-Formylphenylboronic Acid → 4-{6-[(3,4,5-Trimethoxyphenyl)amino]pyrazin-2-yl}benzaldehyde

HRID 16254

Reaction equation

HRID 16254 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16]([C:26]3[CH:27]=[CH:28][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=3)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

Product 1

HCID 117103404-{6-[(3,4,5-Trimethoxyphenyl)amino]pyrazin-2-yl}benzaldehydeYield 61.7%

Procedure

Using Method C with 200 mg (0.68 mmol) 2a and 123 mg (0.82 mmol) 4-formylphenylboronic acid, 153 mg (61.7%) pure title compound were obtained after preparative HPLC (eluent: AcOEt) purification of the whole batch. Reaction time: 24 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 3.64 (s, 3H, CH3O(4′)), 3.83 (s, 6H, CH3O(3′+5′)), 7.25 (s, 2H, Harom(2+6)), 8.05 (d, 2H, Harom 2′+6′, J=8.22), 8.23 (s, 1H, HP5), 8.35 (d, 2H, Harom3′+5′), 8.64 (s, 1H, HP3), 9.68 (s, 1H, NHamine), 10.08 (s, 1H, CHO); MS, (C20H19N3O4), m/z: 395 [M++1, 100].

Sources & evidence

ORD record
ord-af231bab58f548f49891160e4d56d157
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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