4-Methoxy-2-(trifluoromethyl)phenylboronic acid → HCID 23629964, compound

HRID 2375600Notes

Reaction equation

HRID 2375600 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:26]=[CH:25][C:24](B(O)O)=[C:23]([C:30]([F:33])([F:32])[F:31])[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][C:23]=3[C:30]([F:31])([F:32])[F:33])[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 121094604-Methoxy-2-(trifluoromethyl)phenylboronic acidHCID 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamide

Product 1

HCID 23629964HCID 23629964, compoundYield 82%

Procedure

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (116 mg, 0.375 mmol) and [4-methoxy-2-(trifluoromethyl)phenyl]boronic acid (164 mg, 0.75 mmol) were reacted to afford the title compound (124 mg, 82% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.02 (t, J=6.0 Hz, 1H), 8.45 (d, J=8.3 Hz, 1H), 7.67-7.78 (m, 2H), 7.26-7.38 (m, 3H), 3.91 (s, 3H), 3.29 (apparent q, J=7.0 Hz, 2H), 1.57 (apparent sextet, J=7.0 Hz, 2H), 0.90 (t, J=7.0 Hz, 3H). MS APCI, m/z=405 (M+H) HPLC 2.11 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-50e17d1b9f2846a99e0f90731eb5a8e2
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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