4-Chlorophenylboronic acid → HCID 11326288, compound

HRID 1813980Notes

Reaction equation

HRID 1813980 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.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:23][CH2:24][CH3:25])=[C:13]([C:15]2[CH:16]=[C:17]([NH2:22])[N:18]=[C:19]([NH:21][C:30]3[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=3)[CH:20]=2)[CH:14]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 69424824HCID 69424824, compound

Product 1

HCID 11326288HCID 11326288, compoundYield 30%

Procedure

Following the method described in Example 8, 4-(5-chloro-2-ethoxy-phenyl)-pyridine-2,6-diamine trifluoroacetic acid salt and 4-chloro-phenylboronic acid provided the title compound (30% yield). 1H NMR (acetone-d6) δ1.35 (t, 3H, J=7.0 Hz, CH3), 4.08 (q, 2H, J=7.0 Hz, CH2), 5.32 (bs, 2H, NH2), 6.21 (d, 1H, J=1H, J=1.2 Hz, Ar), 6.32 (t, 1H, J=1.1 Hz, Ar), 7.09 (d, 2H, J=8.6 Hz, Ar), 7.23 (d, 2H, J=8.9 Hz, Ar), 7.31-7.78 (m, 2H, Ar), 8.04 (s, 1H, NH).

Sources & evidence

ORD record
ord-79f2d5f28dea4c53957228ceb372297c
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

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