3,5-Dibromo-1-methylpyridin-2(1H)-one → HCID 118022655, compound

HRID 575855Notes

Reaction equation

HRID 575855 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH:11]([Mg]Br)([CH3:13])[CH3:12]>>[Br:8][C:6]1[CH:7]=[C:2]([CH:11]([CH3:13])[CH3:12])[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

Participants

3

Reactant 2

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 178418365HCID 178418365, compound

Product 1

HCID 118022655HCID 118022655, compound

Procedure

Examples 512-514 as described in Table 23 were prepared in three steps. Using conditions similar to those described by Malhotra, et. al. in Organic Letters 2013, Vol. 15, No. 14, pp. 3698-3701 (supporting information, compounds 4c and 3a), 3,5-dibromo-1-methylpyridin-2-one was alkylated at the 3-position using isopropylmagnesium bromide to give 5-bromo-1-methyl-3-propan-2-ylpyridin-2-one which was then reacted with 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane using conditions similar to those described in Example 248, step 2 to give the pinacol ester, 1-methyl-3-propan-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one. This pinacol ester was then substituted for the pinacol ester of the example shown under Synthetic Method in Table 23 and reacted in the same way as the example to obtain the title compounds.

Workup

  1. customwere prepared in three steps

Sources & evidence

ORD record
ord-6e7f25175e294085a0678f8006173542
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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