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

HRID 2375687Notes

Reaction equation

HRID 2375687 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][CH:16]1[CH2:19][CH2:18][CH2:17]1)=[O:14].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:22]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:22]3[C:23]([O:27][CH3:28])=[CH:24][CH:25]=[CH:26][C:21]=3[F:20])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH:16]1[CH2:19][CH2:18][CH2:17]1)=[O:14]

Participants

3

Reactant 2

HCID 3294524(2-Fluoro-6-methoxyphenyl)boronic acidHCID 672284794-amino-8-bromo-N-cyclobutyl-cinnoline-3-carboxamide

Product 1

HCID 236296984-amino-N-cyclobutyl-8-(2-fluoro-6-methoxyphenyl)cinnoline-3-carboxamideYield 19.3%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclobutyl-cinnoline-3-carboxamide (145 mg) and 2-fluoro-6-methoxy-phenyl boronic acid (191 mg) were reacted to afford the title compound (32 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.20 (d, 1H), 8.44 (m, 1H), 7.76 (m, 2H), 7.44 (m, 1H), 6.99 (d, 1H), 6.90 (t, 1H), 4.49 (m, 1H), 3.65 (s, 3H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=367 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fb8fa1130ec743a3b3dab2557ddb2c08
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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