Tolylboronic acid → HCID 69421984, compound

HRID 1813979Notes

Reaction equation

HRID 1813979 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.B(O)(O)[C:27]1[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:23][CH2:24][CH3:25])=[C:13]([C:15]2([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[CH:16]=[C:17]([NH2:22])[N:18]=[C:19]([NH2:21])[CH2:20]2)[CH:14]=1

Participants

3

Reactant 2

HCID 79799Tolylboronic acidHCID 69424824HCID 69424824, compound

Product 1

HCID 69421984HCID 69421984, compoundYield 17%

Procedure

Following the method described in Example 8, 4-(5-chloro-2-ethoxy-phenyl)-pyridine-2,6-diamine trifluoroacetic acid salt and p-tolylboronic acid provided the title compound (17% yield). 1H NMR (acetone-d6) δ1.35 (t, 3H, J=7.0 Hz, CH3), 2.27 (s, 3H, CH3), 4.08 (q, 2H, J=7.0 Hz, CH2), 5.24 (bs, 2H, NH2), 6.14 (d, 1H, J=1.0 Hz, Ar), 6.32 (t, 1H, J=0.9 Hz, Ar), 7.06-7.10 (m, 3H, Ar), 7.29-7.34 (m, 2H, Ar), 7.51-7.54(m, 2H, Ar), 7.67 (s, 1H, NH).

Sources & evidence

ORD record
ord-0049891ecc12444aa221c5c666be19e7
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

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