4-Formylphenylboronic Acid → HCID 11268641, compound

HRID 1813981Notes

Reaction equation

HRID 1813981 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:23][CH2:24][CH3:25])=[C:13]([C:15]2[CH:20]=[C:19]([NH2:21])[N:18]=[C:17]([NH2:22])[CH:16]=2)[CH:14]=1.[CH:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)=[O:27]>>[NH2:22][C:17]1[N:18]=[C:19]([NH:21][C:31]2[CH:32]=[CH:33][C:28]([CH:26]=[O:27])=[CH:29][CH:30]=2)[CH:20]=[C:15]([C:13]2[CH:14]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=2[O:23][CH2:24][CH3:25])[CH:16]=1

Participants

3

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 69424824HCID 69424824, compound

Product 1

HCID 11268641HCID 11268641, compoundYield 22%

Procedure

Following the method described in Example 8, 4-(5-chloro-2-ethoxy-phenyl)-pyridine-2,6-diamine trifluoroacetic acid salt and 4-formyl-phenylboronic acid provided the title compound (22% yield). 1H NMR (acetone-d6) δ1.36 (t, 3H, J=6.9 Hz, CH3), 4.11 (q, 2H, J=7.0 Hz, CH2), 5.51 (bs, 2H, NH2), 6.33 (d, 1H, J=1.1 Hz, Ar), 6.44 (d, 1H, J=1.0 Hz, Ar), 7.12 (d, 1H, J=8.5 Hz, Ar), 7.31-7.37 (m, 2H, Ar), 7.78 (d, 2H, J=8.8 Hz, Ar), 7.88-7.97 (m, 2H, Ar), 8.57 (s, 1H, NH), 9.84 (s, 1H, CH).

Sources & evidence

ORD record
ord-e314df2c155e4488aaffa582c3d0ebd4
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

Loading…