Phenylboronic Acid → HCID 23629934, compound

HRID 2375594Notes

Reaction equation

HRID 2375594 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:15]([NH:17][CH2:18][CH2:19][CH3:20])=[O:16].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:15]([NH:17][CH2:18][CH2:19][CH3:20])=[O:16]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 67228247HCID 67228247, compound

Product 1

HCID 23629934HCID 23629934, compoundYield 52%

Procedure

Using Method F, 4-amino-7-methoxy-8-iodo-N-propyl-cinnoline-3-carboxamide (311 mg, 0.81 mmol) and phenylboronic acid (394 mg, 3.24 mmol) were reacted (refluxed overnight) to afford the title compound (140 mg, 52% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.51 (bm, 1H), 7.90 (d, J=9.2 Hz, 1H), 7.52 (d, J=9.2 Hz, 1H), 7.36-7.50 (m, 5H), 3.92 (s, 3H), 3.43 (apparent q, J=6.4 Hz, 2H), 1.63 (apparent sextet, J=7.2 Hz, 2H), 0.98 (t, J=7.4 Hz, 3H). MS APCI, m/z=337 (M+H) HPLC 1.76 min.

Workup

  1. customwere reacted
  2. temperature(refluxed overnight)

Sources & evidence

ORD record
ord-c914e299d0cd430ab96e0bc91f735e6b
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

Loading…