(4-Methoxyphenyl)boronic acid → HCID 25132773, compound

HRID 31104Notes

Reaction equation

HRID 31104 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:24]3[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14]

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 140123274-amino-8-iodo-N-propyl-cinnoline-3-carboxamide

Product 1

HCID 25132773HCID 25132773, compoundYield 70.2%

Procedure

Using method F, 4-amino-8-iodo-N-propyl-cinnoline-3-carboxamide (178 mg, 0.50 mmol) and 4-methoxyphenylboronic acid (303 mg, 2.00 mmol) were reacted (reflux 14 hours) to afford the title compound (118 mg, 70% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.58 (bm, 1H), 7.69-7.83 (m, 3H), 7.62 (d, J=8.9 Hz, 2H), 7.05 (d, J=8.9 Hz, 2H), 3.87 (s, 3H), 3.45 (apparent q, J=6.6 Hz, 2H), 1.65 (apparent sextet, J=7.4 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H).

Workup

  1. customwere reacted
  2. temperature(reflux 14 hours)

Sources & evidence

ORD record
ord-56fdc0a3626241f985b2bcd8d75d047c
Source dataset
uspto-grants-2008_09
Patent number
US07425556B2

Reaction notes

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