5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester → HCID 178424681, compound

HRID 1488118Notes

Reaction equation

HRID 1488118 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][CH2:8][C:9]#[N:10])[NH:5][CH:6]=1.[CH3:11][C:12]1[CH:21]=[C:20]([CH3:22])[C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:13]=1[C:14]([O:16]C)=O.CC1C=CC(C(OC)=O)=CC=1B1OC(C)(C)C(C)(C)O1.Cl.[F:53][C:54]1([C:58]2[CH:65]=[CH:64][C:61]([C:62]#[N:63])=[CH:60][CH:59]=2)[CH2:57][NH:56][CH2:55]1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[C:9]([CH2:8][CH2:7][C:4]1[NH:5][C:6]([C:19]2[C:20]([CH3:22])=[CH:21][C:12]([CH3:11])=[C:13]([CH:18]=2)[C:14]([N:56]2[CH2:55][C:54]([C:58]3[CH:59]=[CH:60][C:61]([C:62]#[N:63])=[CH:64][CH:65]=3)([F:53])[CH2:57]2)=[O:16])=[C:2]([CH3:1])[N:3]=1)#[N:10]

Participants

6

Reactant 5

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 178430871HCID 178430871, compound2×

Product 1

HCID 178424681HCID 178424681, compound

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5, except 3-(4-methyl-1H-imidazol-2-yl)propanenitrile (compound 232.4) was used in place of 2,4-dimethyl-1H-imidazole, 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+) 442 (M+H)+.

Sources & evidence

ORD record
ord-56a2a734324244d29e18d45dc6e53738
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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