3,5-Dibromo-1-methylpyridin-2(1H)-one → HCID 86661237, compound

HRID 1772134Notes

Reaction equation

HRID 1772134 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[CH:14][C:13]([NH2:16])=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Br:24])[CH:23]=1>>[Br:24][C:22]1[CH:23]=[C:18]([NH:16][C:13]2[CH:14]=[CH:15][N:11]([CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[N:12]=2)[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=1

Participants

3

Reactant 2

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 593449471-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine

Product 1

HCID 86661237HCID 86661237, compoundYield 76%

Procedure

Using the same general procedure as described for the preparation of 103l, reaction of 119b (400 mg, 1.66 mmol) with 3,5-dibromo-1-methylpyridin-2(1H)-one (441 mg, 1.66 mmol) gave a 76% yield (521 mg) of 119c as a yellow solid: mp 96-97° C.; 1H NMR (500 MHz, CDCl3) δ 7.85 (d, 1H, J=2.5 Hz), 7.42 (s, 1H), 5.31 (d, 1H, J=2.5 Hz), 6.87 (d, 1H, J=2.5 Hz), 5.84 (d, 1H, J=2.5 Hz), 4.16 (t, 2H, J=5.0 Hz), 3.96 (t, 2H, J=5.5 Hz), 3.58 (s, 3H), 0.85 (s, 9H), −0.04 (s, 6H). MS (APCI+) m/z 427.4 (M+H).

Sources & evidence

ORD record
ord-6a6f42018cbb47619deca974f3d71f52
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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