2-Bromopropane → 5-Bromo-1-isopropyl-3-methylpyridin-2(1H)-one

HRID 518588Notes

Reaction equation

HRID 518588 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[N:6][CH:7]=1.[CH:10](Br)([CH3:12])[CH3:11]>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5](=[O:8])[N:6]([CH:10]([CH3:12])[CH3:11])[CH:7]=1

Participants

3

Reactant 2

HCID 63582-BromopropaneHCID 178422464HCID 178422464, compound

Product 1

HCID 843175125-Bromo-1-isopropyl-3-methylpyridin-2(1H)-one

Procedure

Examples 508-511 as described in Table 22 were prepared in three steps. Using conditions similar to those described in WO2005/40151 (Preparation 6), 5-bromo-3-methylpyridin-2-ol was N-alkylated with isopropyl bromide to give 5-bromo-3-methyl-1-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, 3-methyl-1-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 22 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-1eb9cbbdb9134a668c6677e307253b34
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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