Phenylboronic Acid → 4-amino-7-fluoro-8-phenyl-N-propyl-cinnoline-3-carboxamide

HRID 2375592Notes

Reaction equation

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

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 59791626HCID 59791626, compound

Product 1

HCID 249059794-amino-7-fluoro-8-phenyl-N-propyl-cinnoline-3-carboxamideYield 26%

Procedure

Using method F, 4-amino-7-fluoro-8-iodo-N-propyl-cinnoline-3-carboxamide (291 mg, 0.78 mmol) and phenylboronic acid (379 mg, 3.11 mmol) were reacted (reflux 4 hours) to afford the title compound (65 mg, 26% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.52 (bs, 1H), 7.89 (dd, J=9.2, 4.6 Hz, 1H), 7.42-7.60 (m, 6H), 3.45 (apparent q, J=6.6 Hz, 2H), 1.65 (apparent sextet, J=7.2 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=325 (M+H) HPLC 1.92 min.

Workup

customwere reacted
temperature(reflux 4 hours)

Sources & evidence

ORD record: ord-b968afde5a3145f098b1e3d2a14b1b93
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465795B2

Reaction notes

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