5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester → HCID 178497346, compound

HRID 1488034Notes

Reaction equation

HRID 1488034 reaction equation
CC1NC(C2C=C(C=CC=2C)C(OC)=O)=C(C)N=1.[CH3:19][C:20]1[CH:29]=[C:28]([CH3:30])[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23].CC1C=CC(C(OC)=O)=CC=1B1OC(C)(C)C(C)(C)O1.I[C:61]1[NH:65][C:64]([C:66]2([CH3:70])[CH2:69][O:68][CH2:67]2)=[N:63][C:62]=1[CH3:71].IC1NC(C)=NC=1C>>[CH3:19][C:20]1[CH:29]=[C:28]([CH3:30])[C:27]([C:61]2[NH:65][C:64]([C:66]3([CH3:70])[CH2:69][O:68][CH2:67]3)=[N:63][C:62]=2[CH3:71])=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 5

HCID 532171365-Methoxycarbonyl-2-methylphenylboronic acid pinacol esterHCID 59224686Methyl 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate2×HCID 178432598HCID 178432598, compound2×HCID 178432771HCID 178432771, compoundHCID 178497719HCID 178497719, compound

Product 1

HCID 178497346HCID 178497346, compound

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5.6, except 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 5-iodo-4-methyl-2-(3-methyloxetan-3-yl)-1H-imidazole (compound 175.2) was used in place of 5-iodo-2,4-dimethyl-1H-imidazole (compound 5.5). m/z (ES+) 315 (M+H)+.

Sources & evidence

ORD record
ord-112d9e9e2d734563a3271cfba99cc6d6
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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