4-Formylphenylboronic Acid → HCID 11348781, compound

HRID 1813983Notes

Reaction equation

HRID 1813983 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.[CH:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:26]>>[NH2:22][C:17]1[N:18]=[C:19]([NH:21][C:30]2[CH:31]=[CH:32][C:27]([CH:25]=[O:26])=[CH:28][CH:29]=2)[CH:20]=[C:15]([C:13]2[CH:14]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=2[O:23][CH3:24])[CH:16]=1

Participants

3

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 69422628HCID 69422628, compound

Product 1

HCID 11348781HCID 11348781, compoundYield 22%

Procedure

Following the method described in Example 8, 4-(5-chloro-2-methoxy-phenyl)-pyridine-2,6-diamine trifluoroacetic acid salt and 4-formyl-phenylboronic acid provided the title compound (22% yield). 1H NMR (acetone-d6) δ3.85 (s, CH3), 5.51 (bs, 2H, NH2), 6.27 (d, 1H, J=1.1 Hz, Ar), 6.38 (d, 1H, J=1.1 Hz, Ar), 7.14 (d, 1H, J=8.8 Hz, Ar), 7.32 (d, 1H, J=2.7 Hz, Ar), 7.38 (dd, 1H, J=8.8 Hz, J=2.7 Hz, Ar), 7.78 (d, 2H, J=8.7 Hz, Ar), 7.96 (d, 2H, J=8.7 Hz, Ar), 8.59 (s, 1H, NH), 9.84 (s, 1H, CH).

Sources & evidence

ORD record
ord-621477db0c7c4bde8f3933d72379fe8e
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

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