5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester → HCID 178423926, compound

HRID 1488217Notes

Reaction equation

HRID 1488217 reaction equation
I[C:2]1[NH:6][N:5]=[C:4]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])[C:3]=1[CH3:12].IC1NC(C)=NC=1C.[CH3:21][C:22]1[CH:31]=[C:30]([CH3:32])[C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][C:23]=1[C:24]([O:26]C)=O.CC1C=CC(C(OC)=O)=CC=1B1OC(C)(C)C(C)(C)O1.Cl.[F:63][C:64]1([C:68]2[CH:75]=[CH:74][C:71]([C:72]#N)=[CH:70][CH:69]=2)[CH2:67][NH:66][CH2:65]1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[F:63][C:64]1([C:68]2[CH:75]=[CH:74][C:71]([CH3:72])=[CH:70][CH:69]=2)[CH2:67][N:66]([C:24]([C:23]2[C:22]([CH3:21])=[CH:31][C:30]([CH3:32])=[C:29]([C:2]3[NH:6][N:5]=[C:4]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])[C:3]=3[CH3:12])[CH:28]=2)=[O:26])[CH2:65]1

Participants

7

Reactant 6

HCID 532171365-Methoxycarbonyl-2-methylphenylboronic acid pinacol esterHCID 552549914-(Azetidin-3-yl)benzonitrile hydrochlorideHCID 59224686Methyl 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate2×HCID 900213344-(3-Fluoroazetidin-3-yl)benzonitrile hydrochloride2×HCID 90029355HCID 90029355, compound2×HCID 178432771HCID 178432771, compound

Product 1

HCID 178423926HCID 178423926, compound

Procedure

The title compound was prepared using the standard chemical manipulations and procedures similar to those used for the preparation of compound 5, except 5-iodo-N,N,4-trimethyl-1H-pyrazole-3-carboxamide (compound 374.2) was used instead of 5-iodo-2,4-dimethyl-1H-imidazole (compound 5.5), methyl 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 160.1) was used in place of methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 5.4) and 4-(3-fluoroazetidin-3-yl)benzonitrile hydrochloride (compound 43.4) was used in place of 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2). m/z (ES+) 460 (M+H)+.

Sources & evidence

ORD record
ord-290bab520baa4affb3d2f3ba0edc1ff0
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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