3,5-Dibromo-1-methylpyridin-2(1H)-one → HCID 178479983, compound

HRID 1772106Notes

Reaction equation

HRID 1772106 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[NH:6][N:5]=2)[CH2:3][CH2:2]1.Br[C:11]1[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=[C:15]([Br:17])[CH:16]=1>>[Br:17][C:15]1[CH:16]=[C:11]([NH:9][C:7]2[NH:6][N:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:8]=2)[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=1

Participants

3

Reactant 2

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 178507266HCID 178507266, compound

Product 1

HCID 178479983HCID 178479983, compoundYield 21%

Procedure

Using the same general procedure as Example 109c, reaction of 3-cyclopropyl-5-amino-1H-pyrazole (500 mg, 4.06 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (1.08 g, 4.06 mmol) afforded a 21% yield (260 mg) of 110a as an off-white solid: mp 203-204° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.20 (s, 1H), 8.02 (d, 1H, J=2.5 Hz), 7.34 (d, 1H, J=2.5 Hz), 5.77 (d, 1H, J=2.1 Hz), 3.48 (s, 3H), 1.84 (m, 1H), 0.90 (m, 4H), 0.63 (m, 4H); MS (ESI+) m/z 309.0 (M+H).

Sources & evidence

ORD record
ord-786c65d88b44459b83631bb25a9f59c4
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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