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

HRID 2375688Notes

Reaction equation

HRID 2375688 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:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:21]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:21]3[C:22]([O:26][CH3:27])=[CH:23][CH:24]=[CH:25][C:20]=3[F:19])[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 3294524(2-Fluoro-6-methoxyphenyl)boronic acidHCID 672292774-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide

Product 1

HCID 597915424-amino-N-cyclopropyl-8-(2-fluoro-6-methoxyphenyl)cinnoline-3-carboxamideYield 60%

Procedure

Using Method H, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (120 mg, 0.39 mmol) and 2-fluoro-6-methoxyphenylboronic acid (250 mg, 1.47 mmol) were reacted (refluxed 2 hours). After purification the title compound (82 mg, 60% yield) was obtained as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.52 (bm, 1H), 7.93 (m, 1H), 7.75 (m, 1H), 7.36 (apparent q, J=7.0 Hz, 1H), 6.84 (m, 2H), 3.69 (s, 3H), 2.96 (m, 1H), 0.85 (m, 2H), 0.63 (m, 2H). MS APCI, m/z=353 (M+H) HPLC 1.74 min.

Workup

  1. customwere reacted
  2. temperature(refluxed 2 hours)

Sources & evidence

ORD record
ord-0e7e815e6bdb492facc10d9244a2fa79
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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