5-broMo-4,6-diMethylpyridin-2-ol synthesis

5synthesis methods

Product Name:5-broMo-4,6-diMethylpyridin-2-ol
CAS Number:89694-55-3
Molecular formula:C7H8BrNO
Molecular Weight:202.05

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Yield:89694-55-3 58%

Reaction Conditions:

Stage #1: 2-amino-5-bromo-4,6-dimethylpyridinewith hydrogenchloride;waterReflux;
Stage #2: with sodium nitrite in water at 20;

Steps:

Intermediate 60{(S)-6-[(R)-4-(1 ,2,4-Trimethyl-6-oxo-1 ,6-dihvdro-pyridin-3-yl)-indan-1 -yloxyl-2,3- dihydro-benzofuran-3-yl)-acetic acid methyl esterStep 1 : 5-bromo-4,6-dimethyl-pyridin-2-ol5-Bromo-4,6-dimethyl-pyridin-2-ylamine (2.01 g) in water (120 mL) and 32% aqueous HCI (40 mL) is heated to reflux temperature and the solution is filtered hot. NaN02 (2.00 g) dissolved in water (40 mL) is added to the hot filtrate with vigorous stirring. The resulting mixture is stirred at room temperature overnight. The mixture is cooled in an ice bath and the precipitate is separated by filtration. The precipitate is washed with water and dried to give the title compound. Yield: 1 .17 g (58% of theory); LC (method 1 ): t_R = 0.82 min; Mass spectrum (EST): m/z = 202/204 (Br) [M+H]⁺.

References:

WO2012/72691,2012,A1 Location in patent:Page/Page column 100

23819-87-6 Synthesis