4-Amino-8-bromo-N-propylcinnoline-3-carboxamide → 4-amino-8-(3,5-dimethoxyphenyl)-N-propyl-cinnoline-3-carboxamide

HRID 31095Notes

Reaction equation

HRID 31095 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][CH2:16][CH2:17][CH3:18])=[O:14].[CH3:19][O:20][C:21]1[CH:22]=[C:23](B2OC(CC)(CC)C(CC)(CC)O2)[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:22]=[C:21]([O:20][CH3:19])[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=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 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamideHCID 693110522-(3,5-Dimethoxyphenyl)-4,4,5,5-tetraethyl-(1,3,2)-dioxaborolane

Product 1

HCID 236300274-amino-8-(3,5-dimethoxyphenyl)-N-propyl-cinnoline-3-carboxamideYield 93.9%

Procedure

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (100 mg, 0.33 mmol) and 2-(3,5-dimethoxyphenyl)-4,4,5,5-tetraethyl-(1,3,2)-dioxaborolane (256 mg, 0.97 mmol) were reacted to afford the title compound (110 mg, 93.9% yield) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.57 (br, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.79 (dd, J=7.2 Hz, J′=1.3 Hz, 1H), 7.71 (t, J=7.7 Hz, 1H), 6.79 (d, 3H), 3.83 (s, 6H), 3.47 (q, J=6.7 Hz, 2H), 1.67 (m, J=7.3 Hz, 2H), 1.01 (t, J=7.4 Hz, 3H) MS APCI, m/z=367 (M+H) HPLC 1.98 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b377d5b7df394722b29933465dc28544
Source dataset
uspto-grants-2008_09
Patent number
US07425556B2

Reaction notes

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