5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester → HCID 178424670, compound

HRID 1488030Notes

Reaction equation

HRID 1488030 reaction equation
CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.I[C:19]1[NH:23][C:22]([CH:24]2[CH2:28][CH2:27][CH2:26][O:25]2)=[N:21][C:20]=1[CH3:29].IC1NC(C)=NC=1C.[CH3:38][C:39]1[CH:48]=[C:47]([CH3:49])[C:46](B2OC(C)(C)C(C)(C)O2)=[CH:45][C:40]=1[C:41]([O:43]C)=[O:42].CC1C=CC(C(OC)=O)=CC=1B1OC(C)(C)C(C)(C)O1>>[CH3:38][C:39]1[CH:48]=[C:47]([CH3:49])[C:46]([C:19]2[NH:23][C:22]([CH:24]3[CH2:28][CH2:27][CH2:26][O:25]3)=[N:21][C:20]=2[CH3:29])=[CH:45][C:40]=1[C:41]([OH:43])=[O:42]

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 178432559HCID 178432559, compound2×HCID 178432711HCID 178432711, compoundHCID 178432771HCID 178432771, compound

Product 1

HCID 178424670HCID 178424670, compound

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5.7, except 5-iodo-4-methyl-2-(tetrahydrofuran-2-yl)-1H-imidazole (compound 173.1) was used in place of 5-iodo-2,4-dimethyl-1H-imidazole (compound 5.5) and 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).

Sources & evidence

ORD record
ord-d53d8a797a1540ad8ea489b787b02047
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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