4-Fluorophenylboronic acid → HCID 23629658, compound

HRID 2375655Notes

Reaction equation

HRID 2375655 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].[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=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 2856454-Fluorophenylboronic acidHCID 140123274-amino-8-iodo-N-propyl-cinnoline-3-carboxamide

Product 1

HCID 23629658HCID 23629658, compoundYield 47%

Procedure

Using method F, 4-amino-8-iodo-N-propyl-cinnoline-3-carboxamide (178 mg, 0.50 mmol) and 4-fluorophenylboronic acid (280 mg, 2.00 mmol) were reacted (reflux 24 hours) to afford the title compound (76 mg, 47% yield) as a white solid. 1H NMR (300 MHz, CDCl3)) δ8.56 (bm, 1H), 7.86 (dd, J=7.7 Hz, 1H), 7.65-7.80 (m, 4H), 7.19 (t, J=8.6 Hz, 2H), 3.45 (apparent q, J=6.6 Hz, 2H), 1.67 (apparent sextet, J=7.4 Hz, 2H), 1.01 (t, J=7.4 Hz, 3H). MS APCI, m/z=325 (M+H) HPLC 1.74 min.

Workup

  1. customwere reacted
  2. temperature(reflux 24 hours)

Sources & evidence

ORD record
ord-8cf741046aea47b5b77adee884777601
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

Loading…