5-Fluoro-2-methoxyphenylboronic acid → HCID 23629804, compound

HRID 2375696Notes

Reaction equation

HRID 2375696 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:15].[F:21][C:22]1[CH:23]=[CH:24][C:25]([O:31][CH3:32])=[C:26](B(O)O)[CH:27]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:24]3[CH:23]=[C:22]([F:21])[CH:27]=[CH:26][C:25]=3[O:31][CH3:32])[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:15]

Participants

3

Reactant 2

HCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 672297344-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide

Product 1

HCID 23629804HCID 23629804, compoundYield 71.1%

Procedure

Using Method A, 4-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide (175 mg) and 5-fluoro-2-methoxy-phenyl boronic acid (191 mg) were reacted to afford the title compound (141 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.21 (d, 1H), 8.53 (m, 1H), 7.74 (m, 1H), 7.28 (m, 1H), 7.17 (m, 2H), 4.49 (m, 1H), 3.64 (s, 3H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=385 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-21f2a17206304b0b8d7c6a45ae121244
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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