(4-Fluoro-2-methoxyphenyl)boronic acid → 4-amino-7-fluoro-8-(4-fluoro-2-methoxy-phenyl)-N-propyl-cinnoline-3-carboxamide

HRID 2375691Notes

Reaction equation

HRID 2375691 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].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=3[O:21][CH3:20])[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

3

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 597916264-amino7-fluoro-8-iodo-N-propylcinnoline-3-carboxamide

Product 1

HCID 532404964-amino-7-fluoro-8-(4-fluoro-2-methoxy-phenyl)-N-propyl-cinnoline-3-carboxamideYield 53%

Procedure

Using method A, 4-amino-7-fluoro-8-iodo-N-propyl-cinnoline-3-carboxamide (250 mg, 0.67 mmol) and (2-methoxy-4-fluorophenyl)boronic acid (227.1 mg, 1.336 mmol) were reacted to afford the title compound (131.7 mg, 53% yield) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 8.49 (bs, 1H), 7.89 (d×d, J=5.5 Hz, J=9.2 Hz, 1H), 7.52 (apparent triplet, J=8.9 Hz, 1H), 7.30 (m, 1H), 6.82 (d×d, J=2.4 Hz, J=8.5 Hz, 1H), 6.79 (d×d, J=2.4 Hz, J=12.8 Hz, 1H), 3.72 (s, 3H), 3.44 (q, J=6.7 Hz, J=13.4 Hz, 2H), 1.64 (apparent sextet, J=7.3 Hz, 2H), 0.99 (t, J=7.6 Hz, 3H). MS APCI, m/z=373 (M+H) HPLC 2.70 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f65ca9258d004dc8b1a7f8798909d78b
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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