(2,5-Dimethylphenyl)boronic acid → 4-amino-8-(2,5-dimethylphenyl)-N-propyl-cinnoline-3-carboxamide

HRID 31096Notes

Reaction equation

HRID 31096 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][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:21]3[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:20]=3[CH3:19])[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 2734347(2,5-Dimethylphenyl)boronic acidHCID 140123274-amino-8-iodo-N-propyl-cinnoline-3-carboxamide

Product 1

HCID 251320654-amino-8-(2,5-dimethylphenyl)-N-propyl-cinnoline-3-carboxamideYield 83.1%

Procedure

Using method B, 4-amino-8-iodo-N-propyl-cinnoline-3-carboxamide (250 mg, 0.702 mmol) and 2,5-dimethylphenylboronic acid (150 mg, 1.00 mmol) were reacted to afford the title compound (195 mg, 83% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.55 (br, 1H), 7.87 (m, 1H), 7.75-7.64 (m, 2H), 7.23-7.07 (m, 3H), 3.44 (apparent quartet, J=7.0 Hz, 2H), 2.35 (s, 3H), 2.01 (s, 3H), 1.64 (apparent sextet, J=7.0 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H) MS APCI, m/z=335 HPLC 1.98 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3021f4145b824f5e8eb4a81d02dc6e73
Source dataset
uspto-grants-2008_09
Patent number
US07425556B2

Reaction notes

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