2,5-Dimethoxyphenylboronic acid → HCID 23629664, compound

HRID 2375673Notes

Reaction equation

HRID 2375673 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[N:8]=[N:9][C:10]2[C:15]([C:16]=1[NH2:17])=[CH:14][CH:13]=[CH:12][C:11]=2Br)=[O:6])[CH:2]=[CH2:3].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1B(O)O>>[CH2:1]([NH:4][C:5]([C:7]1[N:8]=[N:9][C:10]2[C:15]([C:16]=1[NH2:17])=[CH:14][CH:13]=[CH:12][C:11]=2[C:25]1[CH:26]=[C:21]([O:20][CH3:19])[CH:22]=[CH:23][C:24]=1[O:27][CH3:28])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 27343422,5-Dimethoxyphenylboronic acidHCID 67228591HCID 67228591, compound

Product 1

HCID 23629664HCID 23629664, compound

Procedure

The title compound was prepared from 4-amino-8-bromo-cinnoline-3-carboxylic acid allylamide (273 mg, 0.89 mmol) and 2,5-dimethoxyphenyl boronic acid (201.1 mg, 1.11 mmol) according to Method A to afford an off-white solid (105 mg, 32%). 1H NMR (300.132 MHz, CDCl3) δ 8.64 (bs, 1H), 7.87 (d, J=7.3 Hz, 1H), 7.77-7.69 (m, 2H), 6.96 (t, J=2.8 Hz, 1H), 6.96 (s, 1H), 6.93 (d, J=1.8 Hz, 1H), 6.00-5.88 (m, 1H), 5.29 (dq, J=17.2, 1.6 Hz, 1H), 5.17 (dq, J=10.2, 1.4 Hz, 1H), 4.12 (tt, J=5.7, 1.6 Hz, 2H), 3.79 (s, 3H), 3.64 (s, 3H). MS APCI, m/z=365 (M+H). HPLC 1.76 min.

Sources & evidence

ORD record
ord-a1b3136388eb4aac9409b046fb1e18db
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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