Tolylboronic acid → HCID 69421305, compound

HRID 1813978Notes

Reaction equation

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

Participants

Reactant 2

HCID 79799Tolylboronic acid

HCID 69422628HCID 69422628, compound

Product 1

HCID 69421305HCID 69421305, compoundYield 11%

Procedure

Following the method described in Example 8, 4-(5-chloro-2-methoxy-phenyl)-pyridine-2,6-diamine trifluoroacetic acid salt and p-tolylboronic acid provided the title compound (11% yield). 1H NMR (acetone-d6) δ2.26 (s, 3H, CH3), 3.83 (s, 3H, CH3) 5.24 (bs, 2H, NH2), 6.10 (d, 1H, J=1.1 Hz, Ar), 6.26 (t, 1H, J=1.1 Hz, Ar), 7.06 (d, 2H, J=8.5 Hz, Ar), 7.08 (d, 1H, J=8.8 Hz, Ar), 7.29 (d, 1H, J=2.7 Hz, Ar), 7.35 (dd, 1H, J=9.0 Hz, J=3.3 Hz, Ar), 7.53-7.56 (m, 2H, Ar), 7.70 (s, 1H, NH).

Sources & evidence

ORD record: ord-3d0e288ce66b459181e87d1b7a40498a
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875781B2

Reaction notes

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