5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester → Methyl 5-(4-cyano-2-(3-methyloxetan-3-yl)-1H-imidazol-5-yl)-2,4-dimethylbenzoate

HRID 1488085Notes

Reaction equation

HRID 1488085 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[C:71]#[N:72].IC1NC(C)=NC=1C>>[C:71]([C:62]1[N:63]=[C:64]([C:66]2([CH3:70])[CH2:67][O:68][CH2:69]2)[NH:65][C:61]=1[C:27]1[C:28]([CH3:30])=[CH:29][C:20]([CH3:19])=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23])#[N:72]

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 900302075-Iodo-2-(3-methyloxetan-3-yl)-1H-imidazole-4-carbonitrile2×HCID 178432771HCID 178432771, compoundHCID 178497719HCID 178497719, compound

Product 1

HCID 90029557Methyl 5-(4-cyano-2-(3-methyloxetan-3-yl)-1H-imidazol-5-yl)-2,4-dimethylbenzoate

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-2-(3-methyloxetan-3-yl)-1H-imidazole-4-carbonitrile (compound 202.3) was used in place of 5-iodo-2,4-dimethyl-1H-imidazole (compound 5.5). m/z (ES+) 326 (M+H)+.

Sources & evidence

ORD record
ord-8e7306986235460cbe326e0fc644dae3
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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