(2,5-Difluorophenyl)boronic acid → HCID 59791539, compound

HRID 2375694Notes

Reaction equation

HRID 2375694 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].[F:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:25]3[CH:26]=[C:21]([F:20])[CH:22]=[CH:23][C:24]=3[F:27])[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 2734335(2,5-Difluorophenyl)boronic acidHCID 59791626HCID 59791626, compound

Product 1

HCID 59791539HCID 59791539, compoundYield 35%

Procedure

Using method B, 4-amino-7-fluoro-8-iodo-N-propyl-cinnoline-3-carboxamide (150 mg, 0.40 mmol) and (2,5-difluorophenyl)boronic acid (519.0 mg, 3.29 mmol) were reacted to afford the title compound (50.5 mg, 35% yield) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.48 (bs, 1H), 7.96 (d×d, J=5.3 Hz, J=9.3 Hz, 1H), 7.55 (t, J=9.1 Hz, 1H), 7.13-7.23 (m, 3H), 3.45 (apparent q, J=6.9 Hz, J=13.1 Hz, 2H), 1.65 (apparent sextet, J=7.3 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=361 (M+H) HPLC 2.98 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7060bd9cabb94c44ad188171513c7f61
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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