(2-Methoxy-5-methylphenyl)boronic acid → HCID 23629803, compound

HRID 2375695Notes

Reaction equation

HRID 2375695 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].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:24]3[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:23]=3[O:22][CH3:21])[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 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 672297344-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide

Product 1

HCID 23629803HCID 23629803, compoundYield 65.2%

Procedure

Using Method A, 4-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide (175 mg) and 2-methoxy-5-methyl-phenyl boronic acid (187 mg) were reacted to afford the title compound (128 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.18 (d, 1H), 8.50 (m, 1H), 7.71 (m, 1H), 7.24 (m, 1H), 7.07 (m, 1H), 7.03 (m, 1H), 4.49 (m, 1H), 3.61 (s, 3H), 2.29 (s, 3H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=381 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-695260d579194106b1cbd668596a0559
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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