4-Bromo-2-pyridinemethanol

(E)-(1 S, 14R, 15R, 18S, 21 S)-21 -(3-Hydroxy-benzyl)-18-isopropyl-14-methoxy-15-methyl-3-oxa-6, 17, 20, 23, 27-pentaaza-tricyclo[21.3.1.1 *5, 9*]octacosa- 5 7, 9(28), 10-tetraene-2, 16, 19, 22-tetraone; Com ound 17a: (4-Bromo-pyridin-2-yl)-methanol.; Sodium borohydride (763 mg, 20.17 mmol) was added portionwise to a solution of 4- bromo-pyridine-2-carboxylic acid methyl ester (1 .98 g, 9.166 mmol) in ethanol (50 mL) under nitrogen and the reaction mixture was stirred at room temperature for 18 hours. The reaction was quenched by the addition of acetone (10 mL) and the reaction was stirred for 15 minutes. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organics were collected, dried over anhydrous sodium sulfate and the solvent evaporated to afford the title compound (1 .61 g, 94percent) as a yellow oil. H NMR (300 MHz, CDCIStep 1: Triethylamine (1.05 equiv.) was added to a suspension of 4-bromopicolinic acid in benzole (5 mL/mmol), followed by chloroformate (1.05 equiv.) and the reaction mixture stirred 1 h at RT. Triethylamine hydrochloride was filtered out and the filtrate evaporated to low bulk. The anhydride thus obtained was taken up in THF (5 mL/mmol) and added in drops to a suspension of lithium aluminium hydride (1 equiv.) in THF (2 mL/mmol) at -78° C. The mixture was stirred for 30 min. at -78° C., then sat. Na2, 2, 2-trifluoroacetic anhydride (34 mL, 244 mmol) was slowly added to a solution of 4-bromo-2-methylpyridine 1-oxide (9.8 g, 0.052 mol) in dry dichloromethane (100 mL) at 0 °C under NAt a temperature of less than 40 ° C, Dissolve 1300 g of Cpd 2 in 7 L of ethanol.Add 400g of sodium borohydride in batches, Stir at room temperature overnight;2N hydrochloric acid was added dropwise at a temperature of less than 20 ° C to adjust the pH to weakly alkaline, Rotate most of the ethanol, add water, Adjusted to strong alkaline with potassium carbonate, Extracted with ethyl acetate (EA), Wash the product to the aqueous phase with 1N hydrochloric acid.Extracted with EA, The aqueous phase is added with potassium carbonate to adjust to strong alkalinity, EA extraction, sodium chloride washing, Dry over anhydrous sodium sulfate and spin dry.Through the column, 4-bromopyridine-2-methanol (Cpd 3) 650 g was obtained. The yield was 62percent.Preparation 76

Molecular Weight:188.02
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:186.96328
Monoisotopic Mass:186.96328
Topological Polar Surface Area:33.1
Heavy Atom Count:9
Complexity:89.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes