(2-Fluoro-6-methoxyphenyl)boronic acid → 4-amino-N-ethyl-8-(2-fluoro-6-methoxy-phenyl)cinnoline-3-carboxamide

HRID 2375684

Reaction equation

HRID 2375684 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:20]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:20]3[C:21]([O:25][CH3:26])=[CH:22][CH:23]=[CH:24][C:19]=3[F:18])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14]

Participants

3

Reactant 2

HCID 3294524(2-Fluoro-6-methoxyphenyl)boronic acidHCID 672286714-Amino-8-bromo-N-ethyl-cinnoline-3-carboxamide

Product 1

HCID 236296964-amino-N-ethyl-8-(2-fluoro-6-methoxy-phenyl)cinnoline-3-carboxamide

Procedure

Using Method A, 4-amino-8-bromo-N-ethyl-cinnoline-3-carboxamide and 2-fluoro-6-methoxy-phenyl boronic acid were reacted to afford the title compound as a off-white solid. 1H NMR (500 MHz, CDCl3) δ 8.50 (br, 1H), 7.90 (m, 1H), 7.74 (m, 2H), 7.36 (m, 1H), 6.84 (m, 2H), 3.70 (s, 3H), 3.52 (m, 2H), 1.25 (t, J=7.0 Hz, 3H). MS APCI, m/z=341 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b6ab090350f04c46b4a5ca88bbe78846
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Linked notes

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