5-Fluoro-2-methoxyphenylboronic acid → HCID 59791534, compound

HRID 2375715Notes

Reaction equation

HRID 2375715 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[CH2:18][CH2:17]1)=[O:14].[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:29][CH3:30])=[C:24](B(O)O)[CH:25]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:22]3[CH:21]=[C:20]([F:19])[CH:25]=[CH:24][C:23]=3[O:29][CH3:30])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14]

Participants

3

Reactant 2

HCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 672292774-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide

Product 1

HCID 59791534HCID 59791534, compoundYield 76%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (143 mg, 0.47 mmol) and 5-fluoro-2-methoxyphenylboronic acid (158 mg, 0.94 mmol) were reacted. After purification the title compound (125 mg, 76% yield) was obtained as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.54 (bm, 1H), 7.87 (a dd, J=3.1, 6.6 Hz, 1H), 7.73 (m, 2H), 7.10(m, 2H), 6.95 (m, 1H), 3.66 (s, 3H), 2.96 (m, 1H), 0.86 (m, 2H), 0.64 (m, 2H). MS APCI, m/z=353.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-58f8b5d412354bf687c657d5cfccac24
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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