3,5-Dimethyl-4-methoxyphenylboronic acid → HCID 25133104, compound

HRID 2375657Notes

Reaction equation

HRID 2375657 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[C:26]([CH3:27])=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[CH3:31]>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:24]3[CH:25]=[C:26]([CH3:27])[C:21]([O:20][CH3:19])=[C:22]([CH3:31])[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 38175863,5-Dimethyl-4-methoxyphenylboronic acidHCID 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamide

Product 1

HCID 25133104HCID 25133104, compoundYield 83%

Procedure

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (125 mg, 0.40 mmol) and (4-methoxy-3,5-dimethylphenyl)boronic acid (144 mg, 0.80 mmol) were reacted to afford the title compound (121 mg, 82% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ8.57 (bs, 1H), 7.66-7.85 (m, 3H), 7.32 (s, 2 H), 3.78 (s, 3H), 3.46 (apparent q, J=6.6 Hz, 2H), 2.36 (s, 6H), 1.67 (apparent sextet, J=7.2 Hz, 2H), 1.01 (t, J=7.4 Hz, 3H). MS APCI, m/z=365 (M+H) HPLC 2.08 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-14f5879440f849a39d1cefd3fa306ecf
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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